Literature DB >> 16876403

Structure-based drug design of a highly potent CDK1,2,4,6 inhibitor with novel macrocyclic quinoxalin-2-one structure.

Nobuhiko Kawanishi1, Tetsuya Sugimoto, Jun Shibata, Kaori Nakamura, Kouta Masutani, Mari Ikuta, Hiroshi Hirai.   

Abstract

The design of a novel series of cyclin-dependent kinase (CDK) inhibitors containing a macrocyclic quinoxaline-2-one is reported. Structure-based drug design and optimization from the starting point of diarylurea 2, which we previously reported as a moderate CDK1,2,4,6 inhibitor [J. Biol.Chem.2001, 276, 27548], led to the discovery of potent CDK1,2,4,6 inhibitor that were suitable for iv administration for in vivo study.

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Year:  2006        PMID: 16876403     DOI: 10.1016/j.bmcl.2006.07.026

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  11 in total

1.  Cell death induction in resting lymphocytes by pan-Cdk inhibitor, but not by Cdk4/6 selective inhibitor.

Authors:  Makiko Kobayashi; Ikuko Takahashi-Suzuki; Toshiyasu Shimomura; Yoshikazu Iwasawa; Hiroshi Hirai
Journal:  Invest New Drugs       Date:  2010-06-04       Impact factor: 3.850

2.  Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2-b]indazoles: an effective route to 1H-indazolones.

Authors:  Michael B Donald; Wayne E Conrad; James S Oakdale; Jeffrey D Butler; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  The Davis-Beirut reaction: N1,N2-disubstituted-1H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2H-indazoles.

Authors:  Wayne E Conrad; Ryo Fukazawa; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

4.  Efficient synthesis of highly substituted tetrahydroindazolone derivatives.

Authors:  Angela Scala; Anna Piperno; Francesco Risitano; Santa Cirmi; Michele Navarra; Giovanni Grassi
Journal:  Mol Divers       Date:  2015-03-18       Impact factor: 2.943

5.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

6.  Davis-Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route to N-Aryl 2H-Indazoles.

Authors:  Niklas Kraemer; Clarabella J Li; Jie S Zhu; Julio M Larach; Ka Yi Tsui; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2019-07-24       Impact factor: 6.005

7.  Electrochemical synthesis of N,N'-disubstituted indazolin-3-ones via an intramolecular anodic dehydrogenative N-N coupling reaction.

Authors:  Jessica C Bieniek; Michele Grünewald; Johannes Winter; Dieter Schollmeyer; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2022-06-13       Impact factor: 9.969

8.  Potent anti-tumor activity of a macrocycle-quinoxalinone class pan-Cdk inhibitor in vitro and in vivo.

Authors:  Hiroshi Hirai; Ikuko Takahashi-Suziki; Toshiyasu Shimomura; Kazuhiro Fukasawa; Takumitsu Machida; Toru Takaki; Makiko Kobayashi; Tomohiro Eguchi; Hiroko Oki; Tsuyoshi Arai; Koji Ichikawa; Shinichi Hasako; Tsutomu Kodera; Nobuhiko Kawanishi; Yoko Nakatsuru; Hidehito Kotani; Yoshikazu Iwasawa
Journal:  Invest New Drugs       Date:  2010-01-19       Impact factor: 3.850

9.  Rapid and halide compatible synthesis of 2-N-substituted indazolone derivatives via photochemical cyclization in aqueous media.

Authors:  Hui-Jun Nie; An-Di Guo; Hai-Xia Lin; Xiao-Hua Chen
Journal:  RSC Adv       Date:  2019-04-30       Impact factor: 4.036

10.  Dyedauxiliary Groups, an Emerging Approach in Organic Chemistry. The Case of Arylazo Sulfones.

Authors:  Di Qiu; Chang Lian; Jinshan Mao; Maurizio Fagnoni; Stefano Protti
Journal:  J Org Chem       Date:  2020-10-06       Impact factor: 4.354

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