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

Authors
Abe, N Nabeshima, M Fujii, H Kakehi, A Kageura, Y Konakahara, T
Citation
N. Abe et al., Reductive cyclization of 8-(2-nitrophenyl)-1-azaazulene derivatives; Formation of 6a,7-diazanaphth[3,2,1-c d]azulene and 7H-1,7-diazaindeno[1,2-e]azulene systems, a new DNA intercalater, HETEROCYCLE, 54(1), 2001, pp. 329-339
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
1
Year of publication
2001
Pages
329 - 339
Database
ISI
SICI code
0385-5414(20010101)54:1<329:RCO8DF>2.0.ZU;2-B
Abstract
Reaction of ethyl 2-dimethylamino-8-(2-nitrophenyl)-1-azaazulene-3-carboxyl ate with hexamethylphosphorous triamide gave ethyl 6-dimethylamino-6a, 7-di azanaphth[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 intercala ted to Calf-Thymus DNA and a 12-mer DNA with binding constants K-D = 1.55 x 10(6) and 1.75 x 10(6) M-1, respectively.