海洋吲哚生物碱新型类似物的合成：单（吲哚基）-4-三氟甲基吡啶和双（吲哚基）-4-三氟甲基吡啶作为潜在的抗癌剂

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

作者信息

Xiong W N, Yang C G, Jiang B

机构信息

Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P R China.

出版信息

Bioorg Med Chem. 2001 Jul;9(7):1773-80. doi: 10.1016/s0968-0896(01)00070-0.

DOI:10.1016/s0968-0896(01)00070-0

PMID:11425579

Abstract

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.

摘要

利用2-氯-4-三氟甲基吡啶9、2,6-二氯-4-三氟甲基吡啶6或2,6-二氯-3-氰基-4-三氟甲基吡啶23与N-对甲苯磺酰基-3-吲哚硼酸10之间的铃木交叉偶联反应，合成了单（吲哚基）-4-三氟甲基吡啶和双（吲哚基）-4-三氟甲基吡啶。对它们针对P388和A-549细胞的细胞毒性活性进行了评估，并得出半数抑制浓度（IC50）值。4-三氟甲基-2,6-双[3'-(N-对甲苯磺酰基-6'-甲氧基吲哚基)]吡啶18被确定为该系列中活性最强的化合物。