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

Heterocycles Volume 76 Issue Special issue
published_at 2008-04
2008010086.pdf
[fulltext] 257 KB
Title
Facile synthesis of (2-benzimidazolyl)-1-azaazulenes, (2-benzothiazolyl)-1-azaazulenes, and related compouds and evaluation of their anticancer in vitro activity
Creators Yamauchi Noriko
Creators Fujii Hiroyuki
Creators Kakehi Akikazu
Creators Shiro Motoo
Creators Kurosawa Masaki
Creators Konakahara Takeo
Creators Abe Noritaka
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).
Languages eng
Resource Type journal article
Publishers 日本複素環化学研究所
Date Issued 2008-04
File Version Version of Record
Access Rights open access
Relations
[ISSN]0385-5414
[NCID]AA00663739
[isPartOf] [URI]http://data.heterocycles.jp/
Schools 総合科学実験センター 大学院医学系研究科(理学)