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Indexed by:期刊论文

Date of Publication:2006-07-01

Journal:BIOORGANIC & MEDICINAL CHEMISTRY

Included Journals:SCIE、PubMed

Volume:14

Issue:13

Page Number:4639-4644

ISSN No.:0968-0896

Key Words:acenaphtho[1,2-b]pyrrol-carboxylic acid esters; antitumor; esterification; nucleophilic substitution

Abstract:8-Oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylic acid esters and derivatives were prepared and evaluated for cytotoxicity against A549 and P388 cell lines. Based on a novel chromophore precursor 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile 1, the very insoluble 1 was converted to more soluble esters 5 and a series of 3-amino derivatives from 5 were obtained by mild SNArH reaction between 5 and various amines. The biological evaluation indicated that methyl esters 5a are the most cytotoxic with IC50 values of 0.45 and 0.80 mu M (against A549 and P388, respectively) among the parent esters 5a-5f, but 3-amino derivatives 4b and 4c of 5f with bromine showed the highest activity (with IC50 values of 0.019-0.60 mu M) among the 3-amino derivatives. (c) 2006 Elsevier Ltd. All rights reserved.