Synthesis of novel analogues of marine indole alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents

Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.