Synthesis and Antitumor Evaluation of Thiophene Analogs of Kigelinone

Abstract

The synthesis of kigelinone thiophene analogs and related naphtho[2,3-b] thiophene-4,9-quinones from 2-substituted 4,7-dimethoxybenzo[b]thiophenes via an oxidative deprotection, Diels-Alder, and oxidative aromatization reaction sequence is reported. The 2-substituted naphtho[2,3-b] thiophene-4,9-quinones display significant antitumor activity in the range IC50 1.1-47 mu M on a panel of four distinct human cancer cell lines.