Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid Compounds

作者：Coletti Alessia; Lentini Sara; Conte Valeria; Floris Barbara; Bortolini Olga; Sforza Fabio; Grepioni Fabrizia; Galloni Pierluca^*

来源：Journal of Organic Chemistry, 2012, 77(16): 6873-6879.

DOI：10.1021/jo300985x

A new class of pentacyclic diquinoid compounds has been synthesized with a facile one-pot reaction of two molecules of 2-hydroxynaphthoquinone and 1-bromoalkanes in the presence of ferrocene. These molecules were isolated as enol tautomers that exhibit intramolecular hydrogen bond and extended electronic conjugation as proved by the intense absorption spectrum with a broad band between 400 and 600 nm. The spectroscopic and electrochemical characterization of this new class of compounds has been performed. One of the synthesized diquinoid derivatives showed a significant cytotoxicity with IC50 values of 25-50 mu M against Cisplatin-Resistant SKOV3 and colon carcinoma SW480 cell lines. The results of our study provide a valuable tool to a one-pot synthesis of highly conjugated polyquinones, analogous to important biological systems, with significant antitumoral activity.

• 出版日期2012-8-17