研究者詳細 - 好光　健彦

MISC - 好光　健彦

分割表示 65 件中 1 - 20 件目／全件表示 >>

Red-Light-Promoted Radical Cascade Reaction to Access Tetralins and Dialins Enabled by Zinc(II)porphyrin, A Light-Flexible Catalyst 査読

Yusuke Okanishi, Otoki Takemoto, Sanpou Kawahara, Satoshi Hayashi, Toshikatsu Takanami, Takehiko Yoshimitsu

Organic Letters 2024年4月

Osteopontin promotes age-related adipose tissue remodeling through senescence-associated macrophage dysfunction 査読国際共著国際誌

Daigo Sawaki, Yanyan Zhang, Amel Mohamadi, Maria Pini, Zaineb Mezdari, Larissa Lipskaia, Suzain Naushad, Lucille Lamendour, Dogus Murat Altintas, Marielle Breau, Hao Liang, Maissa Halfaoui, Thaïs Delmont, Mathieu Surenaud, Déborah Rousseau, Takehiko Yoshimitsu, Fawzia Louache, Serge Adnot, Corneliu Henegar, Philippe Gual, Gabor Czibik, Geneviève Derumeaux

JCI Insight 8 ( 8 ) 2023年4月

Radical-Based Route to Functionalized Tetralin: Formal Total Synthesis of (±)-Hamigeran B 国際誌

Yusuke Okanishi, Tohru Ishikawa, Takuya Jinnouchi, Satoshi Hayashi, Toshikatsu Takanami, Hiroshi Aoyama, Takehiko Yoshimitsu

The Journal of Organic Chemistry 88 ( 2 ) 1085 - 1092 2023年1月

Organic redox cascade cyclization of 2-alkynylquinones by ascorbic acid in combination with a copper catalyst and its application to formal synthesis of liphagal 国際共著国際誌

Taejoo Jeong, Yusuke Okanishi, Sora Yotsui, In Su Kim, Takehiko Yoshimitsu

New Journal of Chemistry 47 ( 7 ) 3425 - 3429 2023年

A Virtual Screening Platform Identifies Chloroethylagelastatin A as a Potential Ribosomal Inhibitor 査読国際共著

T. R. Caulfield, K. E. Hayes, Y. Qiu, M. Coban, J. Seok Oh, A. L. Lane, T. Yoshimitsu, L. Hazlehurst, J. A. Copland, H. W. Tun

10 1047 2020年10月

A Virtual Screening Platform Identifies Chloroethylagelastatin A as a Potential Ribosomal Inhibitor 査読国際共著国際誌

Thomas R. Caulfield, Karen E. Hayes, Yushi Qiu, Mathew Coban, Joon Seok Oh, Amy L. Lane, Takehiko Yoshimitsu, Lori Hazlehurst, John A. Copland, Han W. Tun

Biomolecules 10 ( 10 ) 1407 - 1407 2020年10月

記述言語：英語掲載種別：速報，短報，研究ノート等（学術雑誌）出版者・発行元：MDPI AG

Chloroethylagelastatin A (CEAA) is an analogue of agelastatin A (AA), a natural alkaloid derived from a marine sponge. It is under development for therapeutic use against brain tumors as it has excellent central nervous system (CNS) penetration and pre-clinical therapeutic activity against brain tumors. Recently, AA was shown to inhibit protein synthesis by binding to the ribosomal A-site. In this study, we developed a novel virtual screening platform to perform a comprehensive screening of various AA analogues showing that AA analogues with proven therapeutic activity including CEAA have significant ribosomal binding capacity whereas therapeutically inactive analogues show poor ribosomal binding and revealing structural fingerprint features essential for drug-ribosome interactions. In particular, CEAA was found to have greater ribosomal binding capacity than AA. Biological tests showed that CEAA binds the ribosome and contributes to protein synthesis inhibition. Our findings suggest that CEAA may possess ribosomal inhibitor activity and that our virtual screening platform may be a useful tool in discovery and development of novel ribosomal inhibitors.

DOI： 10.3390/biom10101407

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Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation 査読

Eriko Tao, Masaki Inoue, Taejoo Jeong, In Su Kim, Takehiko Yoshimitsu

The Journal of Organic Chemistry 85 ( 14 ) 9064 - 9070 2020年7月

Chemical Syntheses and Biological Studies of Agelastatin A, a Bioactive Marine Heterocycle Gifted from Nature 招待査読

Takehiko Yoshimitsu

HETEROCYCLES 100 ( 11 ) 1735 - 1735 2020年5月

天然物合成における窒素フリーラジカル種の戦略的活用：アゲラスタチンAの全合成査読

好光健彦

有機合成化学協会誌 77 ( 5 ) 472 - 481 2019年5月

Ru(II)-Catalyzed C–H Aminocarbonylation of N-(Hetero)aryl-7-azaindoles with Isocyanates

Jeong, T, Lee, S.-H, Chun, R, Han, S, Han, S.-H, Jeon, Y.-U, Park, J, Yoshimitsu, T, Mishra, N. K, Kim, I.-S

J. Org. Chem. 83 ( 8 ) 4641 - 4649 2018年4月

Visceral Adipose Tissue Drives Cardiac Aging Through Modulation of Fibroblast Senescence by Osteopontin Production 国際共著国際誌

Sawaki, D, Czibik, G, Pini, M, Ternacle, J, Suffee, N, Mercedes, R, Marcelin, G, Surenaud, M, Marcos, E, Gual, P, Clement, K, Hue, S, Adnot, S, Hatem, S. N, Tsuchimochi, I, Yoshimitsu, T, Henegar, C, Derumeaux, G

Circulation 138 ( 8 ) 809 - 822 2018年

Total Synthesis of (-)-Agelastatin A: An SH2’ Radical Azidation Strategy

Tsuchimochi, I, Kitamura, Y, Aoyama, H, Akai, S, Nakai, K, Yoshimitsu, T

Chemical Communications 2018年

2-aminoethoxydiphenyl borate provides an anti-oxidative effect and mediates cardioprotection during ischemia reperfusion in mice

Hirofumi Morihara, Masanori Obana, Shota Tanaka, Ikki Kawakatsu, Daisuke Tsuchiyama, Shota Mori, Hiroshi Suizu, Akiko Ishida, Rumi Kimura, Izuru Tsuchimochi, Makiko Maeda, Takehiko Yoshimitsu, Yasushi Fujio, Hiroyuki Nakayama

PLoS ONE 12 ( 12 ) 650 - 659 2017年12月

記述言語：英語出版者・発行元：Public Library of Science

Excessive levels of reactive oxygen species (ROS) and impaired Ca2+ homeostasis play central roles in the development of multiple cardiac pathologies, including cell death during ischemia-reperfusion (I/R) injury. In several organs, treatment with 2-aminoethoxydiphenyl borate (2-APB) was shown to have protective effects, generally believed to be due to Ca2+ channel inhibition. However, the mechanism of 2-APB-induced cardioprotection has not been fully investigated. Herein we investigated the protective effects of 2-APB treatment against cardiac pathogenesis and deciphered the underlying mechanisms. In neonatal rat cardiomyocytes, treatment with 2-APB was shown to prevent hydrogen peroxide (H2O2) -induced cell death by inhibiting the increase in intracellular Ca2+ levels. However, no 2-APB-sensitive channel blocker inhibited H2O2-induced cell death and a direct reaction between 2-APB and H2O2 was detected by 1H-NMR, suggesting that 2-APB chemically scavenges extracellular ROS and provides cytoprotection. In a mouse I/R model, treatment with 2-APB led to a considerable reduction in the infarct size after I/R, which was accompanied by the reduction in ROS levels and neutrophil infiltration, indicating that the anti-oxidative properties of 2-APB plays an important role in the prevention of I/R injury in vivo as well. Taken together, present results indicate that 2-APB treatment induces cardioprotection and prevents ROS-induced cardiomyocyte death, at least partially, by the direct scavenging of extracellular ROS. Therefore, administration of 2-APB may represent a promising therapeutic strategy for the treatment of ROS-related cardiac pathology including I/R injury.

DOI： 10.1371/journal.pone.0189948

Scopus

PubMed

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Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

Keita Takubo, Ahmed A. B. Mohamed, Takafumi Ide, Kazuyuki Saito, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

JOURNAL OF ORGANIC CHEMISTRY 82 ( 24 ) 13141 - 13151 2017年12月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

The dienone-phenol rearrangement is a useful tool for the synthesis of highly substituted phenols. In our previous study of the rearrangement of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienone under deoxyfluorination conditions, bond migration proceeded with very poor regioselectivity. In this paper, an acid-mediated rearrangement, of O-perfluoroalkylsulfonyl difluorides with regioselective migration toward the beta'-carbon is reported. This method allowed the synthesis of a fluorinated analog of allocolchicinoids with improved total yield. Successful application to other substrates was also demonstrated.

DOI： 10.1021/acs.joc.7b02208

Web of Science

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Compounds, compositions, and methods of agelastatin alkaloids: patent evaluation of WO2015042239 (A1) 国際共著国際誌

Takehiko Yoshimitsu, Han W. Tun

EXPERT OPINION ON THERAPEUTIC PATENTS 27 ( 2 ) 113 - 119 2017年2月

記述言語：英語出版者・発行元：TAYLOR & FRANCIS LTD

Agelastatins are a family of tetracyclic alkaloids isolated from marine sponges. The patent examined in this publication covers the chemical synthesis of agelastatins A to F and eight analogues and their therapeutic use against hematologic malignancies. The claim on the chemical synthesis features a novel biomimetic cyclization of a tricyclic precursor, which streamlines scalable access to agelastatins and their analogues. This new synthetic approach can potentially expedite the research on these compounds for therapeutic use against cancers by making them more easily available. The claim on the therapeutic use against hematologic malignancies is based on the in vitro cytotoxicity against a limited number of cell lines and can be further strengthened by in vivo therapeutic evaluations focusing on specific hematologic malignancies. The comparative evaluation of the cytotoxicities of the natural alkaloids described in the application greatly enhances the understanding of their structure-activity relationships (SARs) relevant to the development of novel medicinal leads. Overall, the patent application is strong and has the potential to advance the rapidly expanding agelastatin research.

DOI： 10.1080/13543776.2017.1273902

Web of Science

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Radical Cyclization Strategies in Total Syntheses of Bioactive Fused Cyclic Natural Products

Takehiko Yoshimitsu

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 74 ( 4 ) 350 - 359 2016年4月

記述言語：日本語掲載種別：書評論文，書評，文献紹介等出版者・発行元：SOC SYNTHETIC ORGANIC CHEM JPN

The present article discusses our recent endeavors on natural product syntheses wherein radical reactions are strategically employed to access fused carbocycles. Particular emphasis is placed on the radical cyclizations that made it possible to establish the unique bond connectivity and functionalities of the target natural products. The radical chemistry-based approaches to platencin and clavilactone B are discussed here to show the utility of titanocene (III)-mediated epoxy enone cyclization, decarboxylative radical cyclization of an alkynyl carboxylic acid derivative with lead (IV) in 1,4-dioxane, and samarium (II)-mediated radical cyclization-fragmentation of an unsaturated keto ester, all of which serve as versatile means to elaborate the natural products.

Web of Science

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Diversity Oriented Synthesis of Allocolchicinoids with Fluoro and/or Oxygen Substituent(s) on the C-Ring from a Single Common Intermediate

Keita Takubo, Kazunori Furutsu, Takafumi Ide, Hiroyuki Nemoto, Yuko Ueda, Kazutake Tsujikawa, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016 ( 8 ) 1562 - 1576 2016年3月

記述言語：英語出版者・発行元：WILEY-V C H VERLAG GMBH

Allocolchicinoids, with a distinct polyoxygenated dibenzocycloheptane skeleton, attract much attention as potential candidate anticancer drugs. In this study, eight C-ring fluorinated analogues of allocolchicinoids, seven C-ring oxygen-substituted analogues, and known compounds N-acetylcolchinol and NSC 51046 were synthesized as racemates from a single common intermediate by using either the deoxyfluorination/migration domino reaction or acid-promoted migration as the key step. Among the products obtained, some of the fluorinated derivatives strongly inhibited the growth of prostate DU145 and pancreas Panc 1 cancer cell lines with efficacy comparable to or better than those of N-acetylcolchinol and NSC 51046. They were also less toxic against a non-cancerous cell line than the known compounds were.

DOI： 10.1002/ejoc.201501624

Web of Science

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生物活性縮環天然物の全合成におけるラジカル環化戦略

好光健彦

有機合成化学協会誌 74 350 - 359 2016年

解説「Grob型環開裂」

有機合成化学協会誌 74 379 - 379 2016年

Total Synthesis of Clavilactone B: A Radical Cyclization− Fragmentation Strategy

H. Suizu, D. Shigeoka, H. Aoyama, T. Yoshimitsu

Org. Lett. 17 ( 1 ) 126 - 129 2015年1月

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