新型1,3,4-噁二唑-2-硫酮衍生物的合成及其抗肿瘤活性

Synthesis and Antitumor Activities of Novel 1,3,4-Oxadiazole-2-thione Derivatives

以手性氨基酸和间甲基苯甲酸(或苯乙酸)为原料,经酯化、缩合、肼解和环合反应合成了12个新型的1,3,4-噁二唑-2-硫酮衍生物(6a^6f或7a^7f),其结构经1H NMR,FT-IR和ESI-MS表征。用MTT法研究了6和7的抗肿瘤活性。结果表明:(2S)-5-(3-甲基苯甲酰胺基)苯乙基-1,3,4-噁二唑-2-硫酮(6f)和(2S)-5-(2-羟基-苯乙酰胺基)乙基-1,3,4-噁二唑-2-硫酮(7b)对红白血病细胞(K562)抑制活性较好。

Twelve novel 1,3,4-oxadiazole-2-thione derivatives（6a - 6f or 7a - 7f） were synthesized by condensation, esterifieation, hydrazinolysis and cyclization, using chiral amino acid and m-meth- ylbenzene or phenyl acetate as materials. The structures were characterized by I H NMR, FT-IR and ESI-MS. The antitumor activities of 6 and 7 against cancer cell （K562） were investigated by MTr method. The results showed that （S） -3-methyl-N- [ 2-phenyl-1 - （ 5-thioxo-4,5-dihydro-1,3,4-oxadi- azol-2-yl） ethyl ] benzamide （6f） and （S） -N- [ 2-hydroxy-1- （ 5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2- yl） ethyl] -2-phenylacetamide（Tb） exhibited better antitumor activities against K562.