Updated on 2025/05/21

写真a

 
Yuichi Ishikawa
 
Organization
Graduate School of Nanobioscience Department of Materials System Science Associate Professor
School of Science Department of Science
Title
Associate Professor
Profile
天然物化学、有機合成化学を基盤として次の2つを主眼に研究を行ってきた。
1、特異な生物活性・構造を有する天然有機化合物の合成
Bryostatin類は、顕著な抗腫瘍活性を有するポリエーテルマクロライドであり、その活性と特異な構造から多くの注目を集めている。それらbryostatin類の中でも最も複雑な構造を有するbryostatin 3の合成を行い、初の全合成を達成することができた(Angew. Chem. Int. Ed. 2000, 39, 2290)。また、同様に強力な抗腫瘍活性をもつマクロライドであるamphidinolide類についても合成研究を行った。その結果、amphidinolide B、G、Hについて、全合成を達成した(Angew. Chem. Int. Ed. 2012, 51, 9877)。
2、合成的手法を用いた新規人工生物活性物質の創製
NF-κB阻害剤として見いだされた9-methylstreptimidoneは、その活性発現機構について未解明のままである。しかしながら、さらなる活性試験に供するためには、より多くの化合物が必要であることから、サンプルの大量供給のための構造の簡略化を目的として各種誘導体を合成し、その活性評価を行った。その結果、新規誘導体DTCM-glutarimideが天然物に匹敵する抗炎症作用を有することを見出した(Bioorg. Med. Chem. Lett. 2009, 19, 1726)。
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Degree

  • Ph. D. ( Keio University )

Research Interests

  • Organic chemistry

  • Natural products chemistry

  • Synthetic Organic Chemistry

  • Biological Organic Chemistry Natural Organic compounds

Research Areas

  • Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules

Education

  • Keio University

    2001.4 - 2004.3

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  • Keio University   Graduate School, Division of Science and Engineering

    - 2004

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  • Keio University

    1999.4 - 2001.3

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  • Keio University   Graduate School, Division of Science and Engineering

    - 2001

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  • Keio University   Faculty of Science and Technology   Department of Chemistry

    1995.4 - 1999.3

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  • Keio University   Faculty of Science and Engineering

    - 1999

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Research History

  • 横浜市立大学 理学部 理学科 生命ナノシステム科学研究科 物質システム科学専攻   准教授

    2019.4

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  • 横浜市立大学 学術院 自然科学系列   国際総合科学部 物質科学コース   准教授

    2014.4 - 2019.3

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  • 横浜市立大学 学術院 自然科学系列   国際総合科学部 物質科学コース   助教

    2011.4 - 2014.3

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  • Keio University   Faculty of Science and Technology, Department of Chemistry   Assistant Professor

    2007.4 - 2011.3

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  • ライプティヒ大学(ドイツ)   アレクサンダー・フォン・フンボルト研究員

    2005.6 - 2007.3

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  • Keio University   Faculty of Science and Technology, Department of Chemistry

    2005.4 - 2005.5

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  • Keio University   Faculty of Science and Technology, Department of Chemistry

    2002.4 - 2005.3

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  • Yokohama City University International College of Arts and Sciences, Department of Materials Science Graduate School of Nanobioscience Department of Materials System Science   Associate Professor

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  • Keio University Faculty of Science and Technology, Department of Chemistry, Faculty of Science and Technology Faculty of Science and Technology, Department of Chemistry   Instructor

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  • Yokohama City University International College of Arts and Sciences Materials Science Graduate School of Nanobioscience Department of Materials System Science   Associate Professor

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Professional Memberships

Papers

  • An efficient enantiospecific synthesis of neuroactive glutamate analogs Reviewed

    Tsukamoto Shuntaro, Itagaki Hiyori, Morokuma Kenji, Miyako Kei, Ishikawa Yuichi, Sakai Ryuichi, Oikawa Masato

    Heterocycles   101 ( 1 )   91 - 98   2020

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    Herein we report improved enantiospecific synthesis and some structure-activity relationships of our heterotricyclic artificial glutamate analogs bearing seven-membered ring for the C-ring. Starting from readily available oxanorbornene rac-3, optically pure (2R)-TKM-107, (2R)-IKM-154, and the antipodes were synthesized in total nine steps for each. Mice in vivo assay indicated that only the (2R)-enantiomer was active in both cases. Behaviors phenotypes observed in the mice assay suggested that these compounds are similar in mode of action to that of IKM-159 but with discrete potency.

    DOI: 10.3987/COM-19-S(F)2

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  • Photoremovable NPEC group compatible with Ns protecting group in polyamine synthesis Reviewed

    MIYAHARA Masayoshi, SHIOZAKI Hiroki, TUKADA Hideyuki, ISHIKAWA Yuichi, OIKAWA Masato

    Tetrahedron Letters   59   4259 - 4262   2018.10

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  • Studies on Aculeines: Synthetic Strategy to the Fully Protected Protoaculeine B, the N‐Terminal Amino Acid of Aculeine B Reviewed

    SHIOZAKI Hiroki, Miyahara Masayoshi, OTSUKA Kazunori, MIYAKO Kei, HONDA Akito, TAKASAKI Yuichi, TAKAMIZAWA Satoshi, TSUKADA Hideyuki, ISHIKAWA Yuichi, SAKAI Ryuichi, OIKAWA Masato

    Org. Lett.   20   3403 - 3407   2018.5

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  • Prins reaction using trioxane for trisubstituted, cis-fused hexahydro-2h-furo [3,2-b] pyran derivative Reviewed

    Oriel Hlokoane, Hiyori Itagaki, Manami Chiba, Taiki Noda, Yuichi Takasaki, Kei Miyako, Ryuichi Sakai, Yuichi Ishikawa, Masato Oikawa

    Heterocycles   96 ( 3 )   453 - 460   2018

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Japan Institute of Heterocyclic Chemistry  

    The construction of cis-fused heterobicyclic system involved in neuroactive natural products such as dysiherbaine has been accomplished by employing Prins strategy using 1,3,5-trioxane as an equivalent for formaldehyde. The reactions allowed stereoselective construction of the trisubstituted cis-fused hexahydro-2H-furo[3,2-b]pyran with maximum yield of 60%.

    DOI: 10.3987/COM-17-13776

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  • A monocyclic neodysiherbaine analog: Synthesis and evaluation Reviewed

    Koichi Fukushima, Yuichi Ishikawa, Ryuichi Sakai, Masato Oikawa

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   26 ( 21 )   5164 - 5167   2016.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Monocyclic analog of neuroexcitatory neodysiherbaine has been designed and stereoselectively synthesized in 0.40% yield over total 24 steps starting from D-ribose, by employing domino aldol-Cannizzaro reaction and stereoselective aldol reaction for construction of two quaternary carbon stereogenic centers at C4 and C6 positions, respectively. The hyperactivity of neodysiherbaine in mice was found to deteriorate in the novel analog, upon intracerebroventricular injection. (C) 2016 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2016.09.074

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  • Synthetic study of strongylophorines: stereoselective construction of the characteristic lactone bridge Reviewed

    Yuya Oikawa, Daiki Uchiyama, Takuya Shirasawa, Masato Oikawa, Yuichi Ishikawa

    TETRAHEDRON LETTERS   57 ( 35 )   3949 - 3951   2016.8

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    Herein, we report an efficient construction of the lactone bridge of strongylophorine-2, which is a meroditerpenoid isolated from Strongylophora durissima and an inhibitor for HIF-1 transcriptional pathway. Starting from dehydroepiandrosterone acetate, the characteristic lactone has been constructed in 5.4% over 18 steps by employing, (1) modified oxy radical-mediated C-H functionalization at the C24 methyl group, and (2) four-step manipulation of C4 quaternary carbon stereogenic center. The lactone synthesized here is expected as a precursor for (8-desmethyl)strongylophorine-2 which is of particular interest in terms of structure-activity relationships in the inhibition of HIF-1 transcriptional pathway. (C) 2016 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2016.07.067

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  • Three-Component, Diastereoselective Prins-Ritter Reaction for cis-Fused 4-Amidotetrahydropyrans toward a Precursor for Possible Neuronal Receptor Ligands Reviewed

    Manami Chiba, Yuichi Ishikawa, Ryuichi Sakai, Masato Oikawa

    ACS COMBINATORIAL SCIENCE   18 ( 7 )   399 - 404   2016.7

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    Here, we report an unprecedented, highly diastereoselective Prins-Ritter reaction of aldehydes, homoallylic alcohols, and nitriles in a three-component coupling reaction for the synthesis of tetra-cis-substituted 4-amidotetrahydropyrans. In this study, the reaction was not only applied for carbohydrate-based heterobicycles but also for more complex heterotricycles, showing acceptable levels of conversion yield (42-97% BRSM) and exclusive diastereoselectivity. Furthermore, the latter heterotricycles were converted to nine analogues of our neuronal receptor ligands IKM-159 and MC-27. An in vivo assay by intracerebroventricular injection in mice suggested that the substituent at C9 of the novel analogues interferes with the molecular interactions with the AMPA receptor, which was originally observed in the complex of IKM-159 and the GluA2 ligand binding domain. Our research has thus shown the power of a multicomponent coupling reaction for the preparation of a structurally diverse compound collection to study structure activity relationships of biologically active small molecules.

    DOI: 10.1021/acscombsci.6b00046

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  • Studies directed toward synthesis of taepeenin D: construction of the C4 stereogenic center and the CD benzofuran rings Reviewed

    Yuichiro Nakazawa, Meri Nagatomo, Tsuyoshi Oikawa, Masato Oikawa, Yuichi Ishikawa

    TETRAHEDRON LETTERS   57 ( 24 )   2628 - 2630   2016.6

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    Taepeenin D is a meroterpenoid isolated from roots and stems of Caesalpinia crista, showing inhibitory activity of Hedgehog signaling pathway. Herein we report selective and short-step construction of two fragments of taepeenin D. First, we demonstrated alkoxy radical-mediated selective functionalization at C19 methyl group for construction of the C4 quaternary carbon stereogenic center. Second, the CD benzofuran rings were constructed in 6 short steps from decalone. The synthesis described herein is not only applicable to total synthesis, but also used for study of the structure-activity relationships of taepeenin D. (C) 2016 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2016.05.005

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  • Asymmetric Organocatalytic Cyclopropanation on Chiral Menthyl Acrylate for the Synthesis of (-)-trans-2-Aminomethylcyclopropanecarboxylic Acid [(-)-TAMP] Reviewed

    Yuka Sugeno, Yuichi Ishikawa, Masato Oikawa

    SYNLETT   25 ( 7 )   987 - 990   2014.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:GEORG THIEME VERLAG KG  

    An enantioselective synthesis of (-)-trans-2-aminomethylcyclopropanecarboxylic acid [(-)-TAMP], a partial agonist for GABAc receptor, has been achieved as the hydrochloride salt in 3.9% overall yield for total eight steps from l-menthol. The synthesis features double asymmetric cyclopropanation that employs cinchona alkaloid derived organocatalyst and l-menthyl chiral auxiliary.

    DOI: 10.1055/s-0033-1340953

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  • First enantioselective total synthesis of (-)-dysibetaine CPa and absolute configurations of natural product Reviewed

    Michihiro Sakai, Yuichi Ishikawa, Satoshi Takamizawa, Masato Oikawa

    TETRAHEDRON LETTERS   54 ( 44 )   5911 - 5912   2013.10

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    Here we report total synthesis of enantiomerically pure dysibetaine CPa, isolated from Micronesian marine sponge and expected to serve as a neuroactive agent. Starting from meso-cyclopropane triester, the synthesis was achieved in 12.8% overall yield over 10 steps including organocatalytic enantioselective solvolysis of meso-succinic anhydride as a key step. This work established the absolute configurations of the natural product as (3R,4R). (C) 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2013.08.113

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  • A Synthesis of (-)-cis-2-Aminomethylcyclopropanecarboxylic Acid [(-)-CAMP] Reviewed

    Masato Oikawa, Yuka Sugeno, Yuichi Ishikawa, Hideyuki Tukada

    SYNLETT   24 ( 7 )   886 - 888   2013.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:GEORG THIEME VERLAG KG  

    An enantioselective synthesis of (-)-cis-2-aminomethylcyclopropanecarboxylic acid [(-)-CAMP] has been achieved in 2.5% total yield over ten steps starting from 2-furaldehyde. The synthesis features diastereoselective cyclopropane formation via diazene, followed by oxime formation and the reduction, for construction of the gamma-aminobutyric acid (GABA) motif.

    DOI: 10.1055/s-0032-1317802

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  • Studies on an (S)-2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic Acid (AMPA) Receptor Antagonist IKM-159: Asymmetric Synthesis, Neuroactivity, and Structural Characterization Reviewed

    Lina Juknaite, Yutaro Sugamata, Kazuya Tokiwa, Yuichi Ishikawa, Satoshi Takamizawa, Andrew Eng, Ryuichi Sakai, Darryl S. Pickering, Karla Frydenvang, Geoffrey T. Swanson, Jette S. Kastrup, Masato Oikawa

    JOURNAL OF MEDICINAL CHEMISTRY   56 ( 6 )   2283 - 2293   2013.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    IKM-159 was developed and identified as a member of a new class of heterotricyclic glutamate analogues that act as AMPA receptor-selective antagonists. However, it was not known which enantiomer of IKM-159 was responsible for its pharmacological activities. Here, we report in vivo and in vitro neuronal activities of both enantiomers of IKM-159 prepared by enantioselective asymmetric synthesis. By employment of (R)-2-amino-2-(4-methoxyphenyl)ethanol as a chiral auxiliary, (2R)-IKM-159 and the (2S)-counterpart were successfully synthesized in 0.70% and 1.5% yields, respectively, over a total of 18 steps. Both behavioral and electrophysiological assays showed that the biological activity observed for the racemic mixture was reproduced only with (2R)-IKM-159, whereas the (2S)-counterpart was inactive in both assays. Racemic IKM-159 was crystallized with the ligand-binding domain of GluA2, and the structure revealed a complex containing (2R)-IKM-159 at the glutamate binding site. (2R)-IKM-159 locks the GluA2 in an open form, consistent with a pharmacological action as competitive antagonist of AMPA receptors.

    DOI: 10.1021/jm301590z

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  • Biology- and diversity-oriented domino reactions for synthesis of AMPA receptor antagonist IKM-159 and analogs Reviewed

    Oikawa M, Kasori Y, Katayama L, Murakami E, Oikawa Y, Ishikawa Y

    Synthesis   45   3106 - 3117   2013

  • 1-Hydroxy-2-methyl-2-propyl Isocyanide (HMPI) as a New Convertible Isocyanide for the Ugi Four-Component-Coupling Reaction Reviewed

    Oikawa Masato, Sugamata Yutaro, Chiba Manami, Fukushima Koichi, Ishikawa Yuichi

    Synlett   24 ( 15 )   2014 - 2018   2013

  • Total Synthesis of (+/-)-Dysibetaine CPa and Analogs Reviewed

    Masato Oikawa, Shota Sasaki, Michihiro Sakai, Yuichi Ishikawa, Ryuichi Sakai

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2012 ( 29 )   5789 - 5802   2012.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    The syntheses of the marine sponge-derived ?-amino carboxylic acid dysibetaine CPa and five analogs in their racemic forms were successfully performed by taking advantage of an electron-withdrawing N-(4-nitrophenyl) group in the cyclopropanation reaction, the reductive ring opening of an imide, and the ethanolysis of an N-Boc-protected imide.

    DOI: 10.1002/ejoc.201200730

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  • Synthesis and biological evaluation of molecular probes based on the 9-methylstreptimidone derivative DTCM-glutarimide Reviewed

    Eisuke Ota, Masatoshi Takeiri, Miyuki Tachibana, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   22 ( 1 )   164 - 167   2012.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Molecular probes based on 3-[(dodecylthiocarbonyl)methyl]glutarimide (DTCM-glutarimide) were synthesized and assessed for inhibitory activity against LPS-induced NO production. Among the probes examined, several derivatives exhibited potential for use in determining the target proteins of DTCM-glutarimide. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2011.11.045

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  • Total Syntheses of Amphidinolides B, G, and H Reviewed

    Akihiro Hara, Ryo Morimoto, Yuki Iwasaki, Tsuyoshi Saitoh, Yuichi Ishikawa, Shigeru Nishiyama

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   51 ( 39 )   9877 - 9880   2012

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    DOI: 10.1002/anie.201204992

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  • Design and synthesis of biotinylated DHMEQ for direct identification of its target NF-kappa B components Reviewed

    Tsuyoshi Saitoh, Masatoshi Takeiri, Yuko Gotoh, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   21 ( 21 )   6293 - 6296   2011.11

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    The design and synthesis of dehydroxymethylepoxyquinomicin (DHMEQ) derivatives were carried out to investigate the intracellular targets. The synthetic biotin probe exhibited membrane permeability and combined selectively with the target protein p65. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2011.08.122

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  • Inhibition of macrophage activation and suppression of graft rejection by DTCM-glutarimide, a novel piperidine derived from the antibiotic 9-methylstreptimidone Reviewed

    Masatoshi Takeiri, Miyuki Tachibana, Ayumi Kaneda, Ayumi Ito, Yuichi Ishikawa, Shigeru Nishiyama, Ryoichi Goto, Kenichiro Yamashita, Susumu Shibasaki, Gentaro Hirokata, Michitaka Ozaki, Satoru Todo, Kazuo Umezawa

    INFLAMMATION RESEARCH   60 ( 9 )   879 - 888   2011.9

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    We have previously synthesized a novel piperidine compound, 3-[(dodecylthiocarbonyl)methyl]glutarimide (DTCM-glutarimide), that inhibits LPS-induced NO production, and in the present research we studied further the anti-inflammatory activity of DTCM-glutarimide in a macrophage cell line and in mice bearing transplanted hearts.
    Mouse macrophage-like RAW264.7 cells were employed for the evaluation of cellular inflammatory activity. DTCM-glutarimide was synthesized in our laboratory. The AP-1 activity was measured by nuclear translocation and phosphorylation. For the heart transplantation experiment, male C57BL/6 (H-2b) and BALB/c (H-2d) mice were used as donor and recipient, respectively. DTCM-glutarimide was administered intraperitoneally.
    DTCM-glutarimide inhibited the LPS-induced expression of iNOS and COX-2 in macrophages; but, unexpectedly, it did not inhibit LPS-induced NF-kappa B activation. Instead, it inhibited the nuclear translocation of both c-Jun and c-Fos. It also inhibited LPS-induced c-Jun phosphorylation. Moreover, it inhibited the mixed lymphocyte reaction in primary cultures of mouse spleen cells; and furthermore, in mice it prolonged the graft survival in heart transplantation experiments.
    The novel piperidine compound, DTCM-glutarimide, was found to be a new inhibitor of macrophage activation, inhibiting AP-1 activity. It also inhibited graft rejection in mice, and thus may be a candidate for an anti-inflammatory agent.

    DOI: 10.1007/s00011-011-0348-z

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  • Synthesis of the C7-26 Fragment of Amphidinolides G and H Reviewed

    Akihiro Hara, Ryo Morimoto, Yuichi Ishikawa, Shigeru Nishiyama

    ORGANIC LETTERS   13 ( 15 )   4036 - 4039   2011.8

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    A new approach to the synthesis of the C7-26 fragment of amphidinolides G and H was developed. In the sequence, the C7-18 portion of this fragment was synthesized using an acetylide coupling protocol, while an Evans alkylation and Sharpless asymmetric dihydroxylation were employed as key steps in construction of the C19-26 subfragment. Finally, both of these units were joined by utilizing an aldol coupling reaction to produce the target C7-26 fragment in good yield.

    DOI: 10.1021/ol201547q

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  • Synthesis of Key Fragments of Amphidinolide Q - A Cytotoxic 12-membered Macrolide Reviewed

    Kohei Kawa, Akihiro Hara, Yuichi Ishikawa, Shigeru Nishiyama

    MOLECULES   16 ( 7 )   5422 - 5436   2011.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    beta-Hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to give the sp(2) methyl group. Derivatization of the L-ascorbic acid derivative by Evans asymmetric alkylation and Peterson olefination provided the latter intermediate. The coupling reaction of the segments was examined.

    DOI: 10.3390/molecules16075422

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  • A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant Reviewed

    Daichi Kajiyama, Keisuke Inoue, Yuichi Ishikawa, Shigeru Nishiyama

    TETRAHEDRON   66 ( 52 )   9779 - 9784   2010.12

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    Carbazoles were successfully synthesized by oxidative cyclization of the corresponding diaryl derivatives using electrochemically generated hypervalent iodine oxidant. Electron-withdrawing nitro and donating methoxy groups at the para position of the acetamide group interfered with cyclization. Glycozoline (8) was successfully synthesized in five steps with 50% overall yield. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2010.11.015

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  • A new NF-kappa B inhibitor based on the amino-epoxyquinol core of DHMEQ Reviewed

    Tsuyoshi Saitoh, Chika Shimada, Masatoshi Takeiri, Mitsuhiro Shiino, Shigeru Ohba, Rika Obata, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   20 ( 19 )   5638 - 5642   2010.10

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    The amino-epoxyquinols 6a and 6b were synthesized as soluble derivatives of an NF-kappa B inhibitor DHMEQ (1). In spite of the opposite configuration from 1, 6b rather than 6a affected the deactivation of NF-kappa B, based on NO secretion and MALDI-TOF MS analysis. It was indicated that 6b inhibited the activation by different manner from that of 1. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2010.08.036

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  • Electrochemical construction of the diaryl ethers: a synthetic approach to o-methylthalibrine Reviewed

    Yu Naito, Takamasa Tanabe, Yuki Kawabata, Yuichi Ishikawa, Shigeru Nishiyama

    TETRAHEDRON LETTERS   51 ( 36 )   4776 - 4778   2010.9

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    Electrochemical dimerization of halogenated p-hydroxyphenylacetic acid derivatives followed by Zn reduction provided the corresponding diaryl ethers. Manipulation of the reduction step using several procedures increased its efficiency, which enabled the construction of o-methylthalibrine, an isoquinoline-class alkaloid. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2010.07.037

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  • A Novel Approach to Indoloditerpenes by Nazarov Photocyclization: Synthesis and Biological Investigations of Terpendole E Analogues Reviewed

    Fatima Churruca, Manolis Fousteris, Yuichi Ishikawa, Margarete von Wantoch Rekowski, Candide Hounsou, Thomas Surrey, Athanassios Giannis

    ORGANIC LETTERS   12 ( 9 )   2096 - 2099   2010.5

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    The application of the Nazarov photocyclization as a mild and efficient method for access to the basic core of novel indoloditerpenoid derivatives is reported. The detailed synthesis of these new analogues of terpendole E, as well as their evaluation as potential inhibitors of KSP, is described.

    DOI: 10.1021/ol100579w

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  • Synthesis of Tetrahydropyrroloiminoquinone Alkaloids Based on Electrochemically Generated Hypervalent Iodine Oxidative Cyclization Reviewed

    Keisuke Inoue, Yuichi Ishikawa, Shigeru Nishiyama

    ORGANIC LETTERS   12 ( 3 )   436 - 439   2010.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    An approach to the synthesis of the tetrahydropyrrololminoquinone alkaloids has been developed and applied to the preparation of N-1-beta-D-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.

    DOI: 10.1021/ol902566p

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  • Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappa B Reviewed

    Tsuyoshi Saitoh, Eriko Suzuki, Arisa Takasugi, Rika Obata, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   19 ( 18 )   5383 - 5386   2009.9

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    Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappa B (NF-kappa B) inhibitor that inhibits DNA binding of NF-kappa B components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappa B indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappa B inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2009.07.120

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  • A synthetic study on gymnastatins F and Q: the tandem Michael and aldol reaction approach Reviewed

    Kyoko Murayama, Takamasa Tanabe, Yuichi Ishikawa, Kensuke Nakamura, Shigeru Nishiyama

    TETRAHEDRON LETTERS   50 ( 26 )   3191 - 3194   2009.7

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    Gymnastatins F (1) and Q (2) were successfully synthesized using the tandem Michael and aldol reaction of the corresponding spirodienones with hemiacetal functions. Inspection of the optical purities of the Substrates suggested that undesired racemization does not proceed during the tandem reaction. Results of theoretical calculations agreed with the ratio of the reaction Outcome. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.01.156

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  • Total synthesis of (+/-)-megistophylline I Reviewed

    Yuko Nishihama, Yuichi Ishikawa, Shigeru Nishiyama

    TETRAHEDRON LETTERS   50 ( 23 )   2801 - 2804   2009.6

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    (+/-)-Megistophylline I (1), carrying a dienone residue in the acridone framework, was synthesized using, the Claisen rearrangement to introduce a prenyl group as a key step. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.03.157

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  • Synthesis and biological evaluation on novel analogs of 9-methylstreptimidone, an inhibitor of NF-kappa B Reviewed

    Yuichi Ishikawa, Miyuki Tachibana, Chino Matsui, Rika Obata, Kazuo Umezawa, Shigeru Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   19 ( 6 )   1726 - 1728   2009.3

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    Synthesis of 9-methylstreptimidone analogs and their inhibitory activities against NF-kappa B (nuclear factor-kappa B) are reported. Among several active derivatives synthesized in this study, 8 with a relatively simple structure, exhibited inhibitory activity against LPS-induced NO production comparable to that of 9-methylstreptimidone. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2009.01.107

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  • Synthesis of a spiroacetal moiety of antitumor antibiotic ossamycin by anodic oxidation Reviewed

    Eriko Honjo, Noriki Kutsumura, Yuichi Ishikawa, Shigeru Nishiyama

    TETRAHEDRON   64 ( 40 )   9495 - 9506   2008.9

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    Synthesis of the spiroacetal moiety (C20-C33) of the antitumor antibiotic ossamycin, is reported. Anodic oxidation of the dithioacetal effected simultaneous removal of the protecting group and acetalization to afford the corresponding 6,6-spiroacetal structure in excellent yield. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2008.07.078

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  • Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent Reviewed

    Takahisa Ogamino, Sayo Ohnishi, Yuichi Ishikawa, Takeshi Sugai, Rika Obata, Shigeru Nishiyama

    SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS   7 ( 2 )   175 - 183   2006.3

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    We have developed an efficient construction of spiro derivatives by anodic oxidation of the corresponding phenols, which enabled synthesis of spiroisoxazoline natural products as well as heliannuols, carrying chroman and benzooxepin structures. In addition to nucleophilic attack of hydroxyl or amino groups to the cation generated electrochemerically, it might be of interest to use a carbonyl oxygen as a nucleophilic center, which would provide hemiacetal-type spiro compounds.
    Gymnastatin A 1 was isolated from the strain of Gymnescella dankaliensis separated from the sponge Halichondria japonica, together with other gymnastatins. This marine natural product consists of the spiro structure between the dienone part including two chlorine atoms, and the tetrahydrofuran ring with a hemiacetal moiety, along with the fatty acid part having an asymmetric carbon center attached with the amino group. As part of our extensive electrochemical investigation of halogenated tyrosine derivatives, synthesis of the acetal-spiro derivatives and its application to gymnastatin A 1 was undertaken to develop further efficient and green sustainable methodology. In these investigations, construction of spiro compounds having hemiacetal moiety, and synthesis of gymnastatin A I was achieved successfully. In addition to the synthesis, biological assessment of synthetic samples was examined. Among them, 3, 5, 14, and 15 showed a wide range of inhibitory activity against Gram-positive, -negative bacteria, fungus, and Mycobacterium. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.stam.2005.10.004

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  • The first total synthesis of SB87-Cl and pestalone, novel bioactive benzophenone natural products Reviewed

    D Iijima, D Tanaka, M Hamada, T Ogamino, Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 28 )   5469 - 5471   2004.7

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    SB87-Cl, an inhibitor of testosterone-5alpha-reductase, and pestalone 2 exhibiting effective antimicrobial activity against MRSA (MIC = 37 ng/mL) and VRE (MIC = 78 ng/mL), were novel bioactive benzophenone natural products. Total synthesis of I and 2 has been successfully accomplished. The common synthetic precursor 18 of I and 2, was Successfully obtained by the coupling of 8 with 12. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.05.063

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  • The first total synthesis and absolute stereochemistry of plakortone G from the Jamaican sponge Plakortis sp. Reviewed

    S Kowashi, T Ogamino, J Kamei, Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 22 )   4393 - 4396   2004.5

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    Total synthesis of plakortone G (1), a secondary metabolite of the Jamaican sponge Plakortis sp., was successfully achieved. The absolute configuration of this molecule was determined by comparison of the synthetic diastereomers with reported data to possess the (4R,8R)-configuration 14. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.03.169

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  • Synthesis of the BCD ring system of azaspiracid: Construction of the trispiro ring structure by the thioether approach Reviewed

    Yuichi Ishikawa, Shigeru Nishiyama

    Tetrahedron Letters   45 ( 2 )   351 - 354   2004.1

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    The synthesis of the BCD ring system of azaspiracid 1 has been attained. Construction of the stereochemistry of the C13 position was successfully controlled by connection between the B ring and the C ring with a sulfur atom. © 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2003.10.161

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  • Synthesis of (+/-)-pyranonaphthoquinone derivatives, a Cdc25A phosphatase inhibitor Reviewed

    A Shimbashi, Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 5 )   939 - 941   2004.1

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    The novel pyranonaphthoquinone 2, carrying Cdc25A phosphatase inhibitory activity, has been successfully synthesized through tricyclic compound 16, which was obtained from 15 by using the intramolecular Michael addition. The precursor 9 was derived from 5-bromoveratraldehyde. (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2003.11.120

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  • Electrochemical synthesis of spiroisoxazole derivatives and its application to natural products Reviewed

    T Ogamino, Y Ishikawa, S Nishiyama

    HETEROCYCLES   61   73 - +   2003.12

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    Efficient synthesis of the trans-spiroisoxazole (1) and its unnatural cis-isomer (2) was accomplished by employing anodic oxidation of 4, followed by Zn(BH4)(2) reduction. This method was applied to an assembly of the carbon framework of zamamistatin (12).

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  • Biological activities of alpha-mangostin derivatives against acidic sphingomyelinase Reviewed

    M Hamada, K Iikubo, Y Ishikawa, A Ikeda, K Umezawa, S Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   13 ( 19 )   3151 - 3153   2003.10

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    Deprenyl and benzofenone-type congeners of alpha-mangostin 1 have been synthesized to understand their role for the inhibitory activity against sphingomyelinase (SMase). While removal of the prenyl group of the right side (11 and 12) caused loss of the selectivity between ASMase (acidic sphingomyelinase) and NSMase (neutral sphingomyelinase), the prenyl group of the left side appeared to increase the inhibitory activities (16 and 17). (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/S0960-894X(03)00719-4

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  • The first direct synthesis of alpha-mangostin, a potent inhibitor of the acidic sphingomyelinase Reviewed

    K Iikubo, Y Ishikawa, N Ando, K Umezawa, S Nishiyama

    TETRAHEDRON LETTERS   43 ( 2 )   291 - 293   2002.1

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    A total synthesis of alpha-mangostin 1a has been achieved. The key cyclization reaction to construct the xanthone framework was undertaken by employing the PPh3-CCl4 conditions. The inhibitory activities of 1a and the benzophenone intermediate 16 against the acidic sphingonlyelinase were discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)02137-2

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  • (+)-3-{(4S,5S)-5-[1,1-dimethyl-2-(phenylthio)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}prop-2-yn-1-ol Reviewed

    H Hosomi, S Ohba, K Ohmori, T Obitsu, Y Ogawa, Y Ishikawa, S Yamamura, S Nishiyama

    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS   56   E142 - E143   2000.4

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    The absolute configuration was determined for the title compound, (+)-C18H24O3S, (I), which was prepared in a synthetic study on the natural products, bryostatins.

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  • (-)-(3S)-4-(2-{[4,4-dimethoxy-6-(benzyloxymethyl) perhydropyran-2-yl]methyl}-1,3-dithian-2-yl)-4-methyl-3-(1,1,2,2-tetramethyl-1-silapropoxy)-pentan-1-ol Reviewed

    H Hosomi, S Ohba, K Ohmori, T Obitsu, Y Ogawa, Y Ishikawa, S Yamamura, S Nishiyama

    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS   56   E140 - E141   2000.4

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    The absolute configuration was determined for the title compound, (-)-C32H56O6S2Si, (I), which was prepared in a synthetic study on the natural products bryostatins. Two independent molecules show similar conformations, except for the orientation of the methoxy groups.

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  • Total synthesis of bryostatin 3 Reviewed

    K Ohmori, Y Ogawa, T Obitsu, Y Ishikawa, S Nishiyama, S Yamamura

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   39 ( 13 )   2290 - 2294   2000

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    DOI: 10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6

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MISC

  • Biology-oriented diverted synthesis of glutamate analogs

    Masato Oikawa, Manami Chiba, Chikako Fujimoto, Yuichi Ishikawa

    AMINO ACIDS   47 ( 8 )   1690 - 1690   2015.8

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  • プロトアーキュレインBの合成研究

    OTSUKA KAZUNORI, ISHIKAWA YUICHI, TAKAMIZAWA SATOSHI, SAKAI RYUICHI, OIKAWA MASATO

    日本化学会講演予稿集   94th ( 4 )   1468   2014.3

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  • Dysibetaine CPa/CPbおよび類縁体の不斉全合成と天然物の絶対立体配置決定

    境倫宏, 田中健斗, 石川裕一, 酒井隆一, 及川雅人

    日本化学会講演予稿集   93rd ( 4 )   1220   2013.3

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  • 天然物をモチーフとしたAMPA受容体阻害剤IKM‐159の不斉合成

    常盤一弥, 菅俣祐太郎, 石川裕一, 酒井隆一, 及川雅人

    日本化学会講演予稿集   92nd ( 4 )   1180   2012.3

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  • 天然物をモチーフにしたAMPA受容体阻害剤IKM‐159の類縁体の合成と活性

    菅俣祐太郎, 常盤一弥, 加曽利祐基, 片山理佐, 村上悦子, 石川裕一, 酒井隆一, 及川雅人

    日本化学会講演予稿集   92nd ( 4 )   1181   2012.3

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  • (±)‐dysibetaine CPaの全合成およびその不斉合成戦略

    境倫宏, 佐々木翔太, 石川裕一, 酒井隆一, SWANSON G.T, 及川雅人

    日本化学会講演予稿集   92nd ( 4 )   1182   2012.3

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  • (±)‐dysibetaine CPaおよび類縁体の全合成

    境倫宏, 佐々木翔太, 石川裕一, 酒井隆一, SWANSON G. T, 及川雅人

    天然有機化合物討論会講演要旨集   53rd   643-648 - 648   2011.9

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  • Structure-activity relationship of NF-kappa B inhibitor DHMEQ and preparation of soluble analog

    Chika Shimada, Tsuyoshi Saito, Yuichi Ishikawa, Shigeru Nishiyama, Kazuo Umezawa

    INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE   26   S11 - S11   2010

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  • Discovery of a novel AP-1 function inhibitor DTCM-glutarimide derived from an antibiotic 9-methylstreptimidone

    Miyuki Tachibana, Yuichi Ishikawa, Shigeru Nishiyama, Kazuo Umezawa

    INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE   24   S6 - S6   2009

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  • The first total synthesis of SB87-Cl and pestalone, novel bioactive benzophenone natural products

    D Iijima, D Tanaka, M Hamada, T Ogamino, Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 28 )   5469 - 5471   2004.7

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    SB87-Cl, an inhibitor of testosterone-5alpha-reductase, and pestalone 2 exhibiting effective antimicrobial activity against MRSA (MIC = 37 ng/mL) and VRE (MIC = 78 ng/mL), were novel bioactive benzophenone natural products. Total synthesis of I and 2 has been successfully accomplished. The common synthetic precursor 18 of I and 2, was Successfully obtained by the coupling of 8 with 12. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.05.063

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  • The first total synthesis and absolute stereochemistry of plakortone G from the Jamaican sponge Plakortis sp.

    S Kowashi, T Ogamino, J Kamei, Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 22 )   4393 - 4396   2004.5

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    Total synthesis of plakortone G (1), a secondary metabolite of the Jamaican sponge Plakortis sp., was successfully achieved. The absolute configuration of this molecule was determined by comparison of the synthetic diastereomers with reported data to possess the (4R,8R)-configuration 14. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.03.169

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  • Synthetic studies on azaspiracid, a novel shellfish poison: Attempts to construct the ABCD ring system

    Y Ishikawa, S Nishiyama

    HETEROCYCLES   63 ( 3 )   539 - 565   2004.3

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    Synthesis of the ABCD ring system of azaspiracid (1) was attempted. Construction of the highly substituted tetrahydrofuran (9) via the Pd(0)-mediated cyclization, followed by spirocyclization afforded trispiro-ring (28), carrying an unnatural ring-junctions. The BCD ring system of 1 was successfully produced by using the bridge of a sulfur atom between the B and C ring to control the spiroacetal center of the C13 position. The stereostructures were unambiguously determined by the NOE experiments.

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  • Synthesis of the BCD ring system of azaspiracid: construction of the trispiro ring structure by the thioether approach

    Y Ishikawa, S Nishiyama

    TETRAHEDRON LETTERS   45 ( 2 )   351 - 354   2004.1

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    The synthesis of the BCD ring system of azaspiracid 1 has been attained. Construction of the stereochemistry of the C-13 position was successfully controlled by connection between the B ring and the C ring with a sulfur atom. (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2003.10.161

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  • Synthesis of (±)-pyranonaphthoquinone derivatives, a Cdc25A phosphatase inhibitor

    Tetrahedorn Letters   45 ( 5 )   939 - 941   2004

  • Synthesis of the ABCD ring system of azaspiracid, a marine poison from Mytilus edulis

    Heterocycles   63 ( 4 )   885 - 893   2004

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  • Biological activities of alpha-mangostin derivatives against acidic sphingomyelinase

    M Hamada, K Iikubo, Y Ishikawa, A Ikeda, K Umezawa, S Nishiyama

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   13 ( 19 )   3151 - 3153   2003.10

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    Deprenyl and benzofenone-type congeners of alpha-mangostin 1 have been synthesized to understand their role for the inhibitory activity against sphingomyelinase (SMase). While removal of the prenyl group of the right side (11 and 12) caused loss of the selectivity between ASMase (acidic sphingomyelinase) and NSMase (neutral sphingomyelinase), the prenyl group of the left side appeared to increase the inhibitory activities (16 and 17). (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/S0960-894X(03)00719-4

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  • Electrochemical Synthesis of Spiroxazole Derivatives and its Application to Natural Products

    Heterocycles   61   73 - 78   2003

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  • The first direct synthesis of alpha-mangostin, a potent inhibitor of the acidic sphingomyelinase

    K Iikubo, Y Ishikawa, N Ando, K Umezawa, S Nishiyama

    TETRAHEDRON LETTERS   43 ( 2 )   291 - 293   2002.1

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    A total synthesis of alpha-mangostin 1a has been achieved. The key cyclization reaction to construct the xanthone framework was undertaken by employing the PPh3-CCl4 conditions. The inhibitory activities of 1a and the benzophenone intermediate 16 against the acidic sphingonlyelinase were discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)02137-2

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  • Total synthesis of bryostatin 3

    K Ohmori, Y Ogawa, T Obitsu, Y Ishikawa, S Nishiyama, S Yamamura

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   39 ( 13 )   2290 - 2294   2000

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    DOI: 10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6

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Presentations

  • ヘッジホッグシグナル伝達経路阻害剤 Taepeenin D の合成研究

    前野 和明, 石川 裕一

    日本化学会第105春季年会(2025)  2025.3 

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  • 新規抗がん剤リード化合物Taepeenin Dの合成研究

    前野和明, 折田悠一, 石川裕一

    第85回有機合成化学協会関東シンポジウム(新潟シンポジウム)  2023.11 

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  • Synthetic Studies on Terpenes with Hedgehog and Wnt Signaling Pathway Inhibitory Activities

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  • Synthetic Studies on Terpenes with Intracellular Signaling Pathway Inhibitory Activity

    2022.3 

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  • Synthetic studies of Haebaruol

    Kotaro Ringa, Yuichi Ishikawa

    2021.3 

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  • Synthetic studies of Scopadulciol

    Arimi Takahashi, Yuichi Ishikawa

    2021.3 

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  • プロトアーキュレイン B の合成研究

    菅原 啓, 石川 裕一, 及川 雅人

    日本化学会第96春季年会  2016.3 

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  • クロマノールの効率的な合成法と、それによるStrongylophorineアナログの合成研究

    白澤卓也, 及川雅人, 石川裕一

    第72回有機合成化学協会関東支部シンポジウム  2016.11 

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  • エナミドのN-アルキル化を鍵反応とするprotoaculeine B の合成研究

    塩﨑宏樹, 石川裕一, 及川雅人

    第72回有機合成化学協会関東支部シンポジウム  2016.11 

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  • Studies on asymmetric synthesis of excitatory agent IKM-154

    ITAGAKI Hiyori, ISHIKAWA Yuichi, OIKAWA Masato

    2017.3 

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  • Pd 触媒を用いたクロマノール構築による HIF-1 活性化経路阻 害剤 Strongylophorine 類の合成研究

    白澤卓也, 及川雅人, 石川裕一

    日本化学会第97春季年会  2017.3 

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  • Synthetic studies on marine natural polyamine protoaculeine-B

    SHIOZAKI, Hiroki, ISHIKAWA Yuichi, OIKAWA Masato

    2017.3 

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  • 新規抗がん剤リード化合物Scopadulciolの合成研究

    樋口博之, 及川雅人, 石川裕一

    第73回有機合成化学協会関東支部シンポジウム  2017.5 

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  • 神経興奮性IKM-154の不斉合成研究

    板垣ひより, 石川裕一, 及川雅人

    第73回有機合成化学協会関東支部シンポジウム  2017.5 

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  • 天然物をモチーフとする神経生理活性化合物の創製の試み

    板垣 ひより, 諸熊 賢治, 石川 裕一, 及川 雅人

    第59回天然有機化合物討論会  2017.9 

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  • シナプス受容体に活性反転を引き起こすリガンドの不斉合成研究

    及川雅人, 板垣ひより, 石川裕一

    日本ケミカルバイオロジー学会第12回年会  2017.6 

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  • Studies on asymmetric synthesis of artificial glutamate analogs having opposite neuronal activities

    TSUKAMOTO Shuntaro, MOROKUMA Kenji, ISHIKAWA Yuichi, OIKAWA Masato

    2018.3 

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  • Synthetic studies of marine polyamine

    MIYAHARA Masayoshi, SHIOZAKI Hiroki, ISHIKAWA Yuichi, OIKAWA Masato

    2018.3 

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  • Skeletal diversity from cis-2-alkenylcycloalkan-1-ol

    NODA Taiki, HLOKOANE Oriel, ISHIKAWA Yuichi, OIKAWA Masato

    2018.3 

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  • 新規抗がん剤リード化合物Scopadulciolの合成研究

    高橋愛梨美, 石川 裕一

    第77回有機合成化学協会関東支部シンポジウム  2019.5 

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  • 新規抗がん剤リード化合物 Taepeenin D の合成研究

    遠藤翔一, 石川 裕一

    第78回有機合成化学協会関東支部シンポジウム  2019.11 

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  • 新規抗がん剤創製を指向したStrongylophorineアナログの合成研究

    白澤卓也, 内山大貴, 及川雅人, 石川裕一

    第109回有機合成シンポジウム  2016.6 

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  • 新規抗がん剤リード化合物 Scopadulciol の合成研究

    高橋 愛梨美, 石川 裕一

    第78回有機合成化学協会関東支部シンポジウム  2019.11 

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  • 新規抗がん剤リード化合物Taepeenin Dの合成研究

    星野莉輝、折田悠一、石川裕一

    第82回有機合成化学協会関東支部シンポジウム  2022.5 

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  • 抗腫瘍性マクロライド化合物amphidinolide B, G, Hの全合成

    原 彰宏, 森本 諒, 岩﨑 祐樹, 仮屋 光馬, 石川 裕一, 西山 繁

    第53回天然有機化合物討論会  2011.9 

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  • DTCM-glutarimideによるマウスメラノーマ細胞の浸潤抑制とanoikis誘導

    兼田 亜弓, 石川 裕一, 西山 繁, 梅澤 一夫

    第52回天然有機化合物討論会  2010.9 

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  • -マンゴスチンとその関連物質の合成と生物活性

    飯久保 一彦, 石川 裕一, 濵田 基子, 田中 大輔, 池田 彩, 梅澤 一夫, 西山 繁

    第44回天然有機化合物討論会  2002.10 

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  • ブリオスタチン類の合成研究

    大森 建, 小櫃 徹夫, 小川 泰之, 石川 裕一, 西山 繁, 山村 庄亮

    第40回天然有機化合物討論会  1998.10 

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  • 電解合成法・タリウム酸化法を駆使したイソジチロシン類の全合成研究

    田邊 貴將, 宇野 加奈子, 森 千春, 内藤 雄, 村山 響子, 小畠 りか, 石川 裕一, 西山 繁

    第50回天然有機化合物討論会  2008.10 

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  • 9-methylstreptimidone由来新規iNOS誘導阻害剤の合成と作用機構

    橘 みゆき, 石川 裕一, 西山 繁, 梅澤 一夫

    第50回天然有機化合物討論会  2008.9 

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  • 新規転写因子AP-1活性阻害剤DTCM-glutarimideの作用機構と生物活性

    兼田 亜弓, 橘 みゆき, 石川 裕一, 西山 繁, 梅澤 一夫

    第51回天然有機化合物討論会  2009.10 

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  • 抗腫瘍性マクロライド化合物amphidinolide類の合成研究

    原 彰宏, 岩﨑 祐樹, 森本 諒, 若松 孝行, 石川 裕一, 西山 繁

    第51回天然有機化合物討論会  2009.10 

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  • (+/-)-dysibetaine CPaおよび類縁体の全合成

    境 倫宏, 佐々木 翔太, 石川 裕一, 酒井 隆一, G. T. Swanson, 及川 雅人

    第53回天然有機化合物討論会  2011.9 

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  • プロトアーキュレインBの合成研究

    大塚 一憲, 石川 裕一, 高見澤 聡, 酒井 隆一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • 光学活性アミンをUgi 4成分連結反応に用いるα-アミノ酸の合成法

    菅俣 祐太郎, 鈴木 雄貴, 石川 裕一, 及川 雅人

    第54回天然有機化合物討論会  2012.9 

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  • 超原子価ヨウ素試薬を活用した含窒素化合物の合成研究

    梶山 大地, 斉藤 毅, 井上 桂輔, 山口 智史, 石川 裕一, 西山 繁

    第54回天然有機化合物討論会  2012.9 

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  • 1-Hydroxy-2-methyl-2-propyl isocyanide による Ugi 反応と post-Ugi 反応

    福島 孝一, 菅俣 祐太郎, 千葉 まなみ, 石川 裕一, 及川 雅人

    第66回有機合成化学協会関東支部シンポジウム  2013.11 

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  • 海綿由来GABA類縁体とその部分構造の合成研究

    菅野 由香, 境 倫宏, 田中 健斗, 石川 裕一, 及川 雅人

    第55回天然有機化合物討論会  2013.9 

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  • 有機触媒による不斉シクロプロパン化と、配座固定アミノ酸合成への応用

    田中 健斗, 菅野 由香, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • 7-Oxanorbornene類のドミノメタセシス反応によるシナプス受容体リガンド候補化合物の合成研究

    千葉 まなみ, 藤本 千賀子, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • Clickableダイシハーベインの合成研究

    福島 孝一, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • Ugi 4成分連結反応を用いた、α,α-二置換アミノ酸の合成研究

    菅俣 祐太郎, 吉岡 広大, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • メロジテルペノイドStrongylophorine類縁体の合成研究

    内山 大貴, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • ダイシベタインCPbの合成研究

    田中 健斗, 石川 裕一, 及川 雅人

    日本化学会第94春季年会  2014.3 

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  • ストロンギロフォリンアナログの合成研究

    内山 大貴, 石川 裕一

    日本化学会第95春季年会  2015.3 

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  • 新規抗がん剤創製を指向したストロンギロフォリンアナログの合成研究

    内山 大貴, 及川 侑也, 石川 裕一, 及川 雅人

    第56回天然有機化合物討論会  2014.10 

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  • 立体選択的 Prins-Ritter 反応によるシナプス受容体リガンドの 合成化学的開発の試み

    千葉 まなみ, 藤本 千賀子, 石川 裕一, 及川 雅人

    日本化学会第96春季年会  2016.3 

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  • プロトアーキュレインBの合成研究

    菅原 啓, 大塚 一憲, 石川 裕一, 及川 雅人

    第57回天然有機化合物討論会  2015.9 

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Research Projects

  • 天然物の活性基本構造を基盤とした新規シグナル伝達経路阻害物質の選択的合成

    Grant number:23K04946  2023.4 - 2026.3

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    石川 裕一

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    Grant amount:\4550000 ( Direct Cost: \3500000 、 Indirect Cost:\1050000 )

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  • 天然由来シグナル伝達経路阻害物質の活性中核構造の解明

    2018.4 - 2022.3

    科研費:基盤研究(C) 

    石川 裕一

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    Authorship:Principal investigator  Grant type:Competitive

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  • 天然有機化合物を基盤とした新規ヘッジホッグシグナル阻害剤の創製

    2013.4 - 2016.3

    科研費  基盤研究(C) 

    石川 裕一

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    Authorship:Principal investigator  Grant type:Competitive

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  • 天然有機化合物を基盤とした新規低酸素誘導因子阻害剤の創製

    2010 - 2011

    科研費 若手研究(B) 

    石川 裕一

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    Authorship:Principal investigator  Grant type:Competitive

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  • 発癌予防薬を指向したオルニチンデカルボキシラーゼ発現阻害剤saliniketal類の合成と構造−活性相関研究

    2008

    服部報公会 工学研究奨励援助 

    石川 裕一

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    Authorship:Principal investigator  Grant type:Competitive

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  • 新規食中毒原因貝毒アザスピロ酸類の合成研究とその作用機作の解明

    2003 - 2004

    科研費 若手研究(B) 

    石川 裕一

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    Authorship:Principal investigator  Grant type:Competitive

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