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- Title
Synthesis and antiproliferative evaluation of new isomeric ellipticine quinones.
- Authors
VALDERRAMA, Jaime A.; IBACACHE, Juana Andrea; THEODULOZ, Cristina
- Abstract
The synthesis of new isomeric ellipticine quinones 3a-c and their in vitro antiproliferative activities on cancer cell lines is reported. The designed N-heterocyclic quinones 3a-c were synthesized through a three step sequence which involves: a) one-pot preparation of 4-methoxycarbonyl-3,4-dimethylisoquinoline-5,8-quinone 1 from 2,5-dihydroxyacetophenone, methyl aminocrotonate and silver (II) oxide; b) regioselective amination of 1 with arylamines to give aminoquinones 2a-c and c) palladium-catalyzed intramolecular oxidative coupling of 7-aminoisoquinoline-5,8-quinones 2a-c. The in vitro antiproliferative activity of the new angular quinones was evaluated againts one normal cell line (lung fibroblasts) and gastric, lung and bladder cancer cell lines in 72-h drug exposure assays. The new compounds displayed similar or higher antiproliferative activity with respect to their quinone precursors 2a-c. The isomeric ellipticine quinone 2b appears as the more active member on bladder cancer cell line (IC50: 2.4 μM), comparable to etoposide used as anticancer reference drug.
- Subjects
QUINONE; AROMATIC compounds; CANCER cells; CELLULAR pathology; ISOMERS
- Publication
Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, 2014, Vol 13, Issue 6, p566
- ISSN
0717-7917
- Publication type
Article