title: Unexpected one-pot synthesis of highly conjugated pentacyclic diquinoid compounds.
abstract: 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 IC(50) 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.
authors: Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma Tor Vergata, Via della Ricerca Scientifica snc, 00133 Roma, Italy.
authors: Alessia
authors: A
authors: Coletti
authors: Sara
authors: S
authors: Lentini
authors: Valeria
authors: V
authors: Conte
authors: Barbara
authors: B
authors: Floris
authors: Olga
authors: O
authors: Bortolini
authors: Fabio
authors: F
authors: Sforza
authors: Fabrizia
authors: F
authors: Grepioni
authors: Pierluca
authors: P
authors: Galloni
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002945:Cisplatin / Q000494:pharmacology; D005296:Ferrous Compounds / Q000737:chemistry*; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D006801:Humans; D006860:Hydrogen Bonding; D000075163:Metallocenes; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000473:Alkanes; D000970:Antineoplastic Agents; D005296:Ferrous Compounds; D000075163:Metallocenes; D009285:Naphthoquinones; D002945:Cisplatin; C005090:lawsone; C004998:ferrocene