Facile synthesis of (2-benzimidazolyl)-1-azaazulenes, (2-benzothiazolyl)-1-azaazulenes, and related compouds and evaluation of their anticancer in vitro activity

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概要

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• Facile syntheses of 2-, 3,- and 8-(2-benzimidazolyl)-1-azaazulenes (2a-c, 5, 7, 9) and 2-, 3-, and 8-(2-benzothiazolyl)-1-azaazulenes (13b-c, 16, 17, 18) were achieved by the condensation of corresponding 1-azaaazulene- carbaldehydes with o-phenylenediamine and 2-aminothiophenol in alcoholic solvents at rt or under reflux under airobic conditions. Reaction of 1-azaazulenecarbaldehyds with 2-aminophenol gave Schiff’s bases (10a-c, 11, 12). Reaction of 2-chloro-1-azaazulene-3-carbaldehyde (1a) with 2-amino- thiophenol in refluxing 1-BuOH gave benzothiazapine-fused 1-azaazulene (20). Reaction of 4-amino-3-mercapto-4H-1,2,4-triazoles (21a-d) with in refluxing 1-BuOH gave triazolothiadizapine-fused 1-azaazulene (22a-d). The structure of trifluolomethyl derivative (22c) was determined by X-ray structure analysis. 3-(2-Benzimidazolyl)-2-chloro-1-azaazulene (2a) showed anticancer activity against HeLa S3 cells (IC_<50>: 5.3 μM).

• 日本複素環化学研究所の論文

著者

• Kakehi A

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Akikazu Kakehi

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Shiro M

  Rigaku Corp. Tokyo

• Fujii Hiroyuki

  Yamaguchi Univ. Yamaguchi Jpn

• Shiro M

  Rigaku Corporation

• Suzuki Mitsuko

  Institute For Chemical Research Kyoto University

• Masuoka S

  Takara Agri Co. Ltd.

• Shiro Motoo

  Shionogi Research Laboratry Shionogi & Co. Ltd.

• Konakahara Takeo

  Faculty Of Science And Technology Tokyo University Of Science (rikadai)

• Mito S

  Institute For Chemical Research Kyoto University

• Abe Noritaka

  Tokyo Univ. Sci. Chiba Jpn

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