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On the chemistry of cinnoline IV {[}1]. Synthesis and reactions of (4-aminocinnolin-3-yl)-aryl-methanones
Faculty
Science
Year:
2001
Type of Publication:
Article
Pages:
859-870
Authors:
AMER, AM
DOI:
10.1007/s007060170075
Journal:
MONATSHEFTE FUR CHEMIE SPRINGER-VERLAG WIEN
Volume:
132
Research Area:
Chemistry
ISSN
ISI:000170528800013
Keywords :
cycloadditions, hydrazones, cinnolines, pyridines, antitumor activity
Abstract:
The synthesis of a series of disubstituted (4-aminocinnolin-3-yl)-aryl-methanones from aryl-hydrazonomalononitrile in a one-step procedure is described. Cyclocondensation of (4-amino-6,8-dimethyl-cinnolin-3-yl)-phenyl-methanone with malononitrile, diethylmalonate, and dimethylacetamide-dimethylacetal gave the corresponding pyrido{[}3,2-c]cinnoline derivatives. Treatment of (4-amino-6,8-dimethyl-cinnolin-3-yl)-phenyl-methanone with triethyl-orthoacetate under reflux readily afforded the corresponding imidoester which underwent cyclization to a pyrido{[}3,2-c]cinnoline derivative. This starting compound could also be annelated to the corresponding 1,2-dihydro-4-aryl-2-oxo-pyrido{[}3,2-c]cinnoline derivatives via the (4-acetamidocinnolin-3-yl)-aryl-methanones. Chemical and spectroscopic evidences for the structures of the new compounds are presented. The effect of three of the compounds against sixty cancer types was tested.
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