Reductive cyclization of 8-(2-nitrophenyl)-1-azaazulene derivatives; formation of 6a,7-diazanaphth[3,2,1-cd]azulene and 7H-1,7-diazaindeno[1,2-e]azulene systems, a new DNA intercalater

Creators Abe Noritaka

Creators Nabeshima Maki

Creators Fujii Hiroyuki

Creators Kakehi Akikazu

Creators Kageura Yuichi

Creators Konakahara Takeo

Reaction of ethyl 2-dimethylamino-8-(2-nitrophenyl)-1-azaazulene-3-carboxylate with hexamethylphosphorous triamide gave ethyl 6-dimethylamino-6a,7-diazanaphth[3,2,1-cd]azulene-5-carboxylate (7b) and ethyl 2-dimethylamino-7H-1,7-diazaindeno[1,2-e]azulene-3-carboxylate (8b). The structures of 7b and 8b were determined by X-Ray structure analyses. Compound (8b) was intercalated to Calf-Thymus DNA and a 12-mer DNA with binding constants K_D=1.55×10^6 and 1.75×10^6 M^<-1>, respectively.

[ISSN]0385-5414

[NCID]AA00663739