Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid Compounds

• Published in: Journal of organic chemistry Vol. 77; no. 16; pp. 6873 - 6879
• Main Authors: Coletti, Alessia, Lentini, Sara, Conte, Valeria, Floris, Barbara, Bortolini, Olga, Sforza, Fabio, Grepioni, Fabrizia, Galloni, Pierluca
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 17-08-2012
• Subjects: Alkanes - chemistry; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Biological and medical sciences; Cell Line, Tumor; Cell Survival - drug effects; Chemistry; Cisplatin - pharmacology; Condensed benzenic and aromatic compounds; Electrochemistry; Exact sciences and technology; Ferrous Compounds - chemistry; Fibroblasts - cytology; Fibroblasts - drug effects; General and physical chemistry; General aspects; Humans; Hydrogen Bonding; Medical sciences; Metallocenes; Naphthoquinones - chemical synthesis; Naphthoquinones - chemistry; Naphthoquinones - pharmacology; Noncondensed benzenic compounds; Organic chemistry; Pharmacology. Drug treatments; Preparations and properties; Stereoisomerism; Structure-Activity Relationship; Antineoplastic agent; Pentacyclic compound; One pot reaction; Transition element complexes; Carcinoma; Quinone; Enol; Cytotoxicity; Naphthoquinone derivatives; Tautomer; Metallocene; Cisplatin; Ferrocene; Characterization; Iron Organic compounds; Absorption spectrometry; Cell line; Electrochemistry; Aromatic compound; Colon; Conjugated compound; Spectrophotometry; Chemical synthesis; Intramolecular hydrogen bond
• ISSN: 0022-3263; 1520-6904
• 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 μM 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.