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 IC(50) values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series.
Xiong
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WN
Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P R China.
Yang
C G
CG
Jiang
B
B
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000470:Alkaloids; D000970:Antineoplastic Agents; D007211:Indoles; D011725:Pyridines