Facile synthesis of (2-Benzimidazolyl)-1-azaazulenes, (2-Benzothiazolyl)-1-azaazulenes, and related compounds 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 (IC50: 5.3 μM).
- 日本複素環化学研究所の論文
著者
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Kakehi A
Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University
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Akikazu Kakehi
Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University
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Shiro M
Rigaku Corp. Tokyo
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Fujii Hiroyuki
Yamaguchi Univ. Yamaguchi Jpn
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Shiro M
Rigaku Corporation
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Suzuki Mitsuko
Institute For Chemical Research Kyoto University
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Masuoka S
Takara Agri Co. Ltd.
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Shiro Motoo
Shionogi Research Laboratry Shionogi & Co. Ltd.
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Konakahara Takeo
Faculty Of Science And Technology Tokyo University Of Science (rikadai)
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Mito S
Institute For Chemical Research Kyoto University
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Abe Noritaka
Tokyo Univ. Sci. Chiba Jpn
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