Facile synthesis of (2-Benzimidazolyl)-1-azaazulenes, (2-Benzothiazolyl)-1-azaazulenes, and related compounds and evaluation of their anticancer in vitro activity

Facile synthesis of (2-Benzimidazolyl)-1-azaazulenes, (2-Benzothiazolyl)-1-azaazulenes, and related compounds 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 (IC50: 5.3 μM).

[ISSN]0385-5414

[NCID]AA00663739

info:doi/10.3987/COM-08-S(N)53

[isVersionOf] [URI]http://www.heterocycles.jp/