3-N-三氟乙酰基-2,5-二芳基-1,3,4-噁唑啉类化合物的合成及抗癌活性研究

Synthesis and antibacterial activity of new 3-trifluoroacetyl-2,5-disubstituted-1,3,4-oxadiazolines

以芳香酸为原料,通过酯化、肼解制得芳基甲酰肼,芳基甲酰肼再与芳香醛反应得到相应的酰腙,最后酰腙与三氟乙酸酐反应脱水环化成标题化合物,并利用IR、1HNMR、13CNMR、ESI-MS和元素分析对8个目标化合物的结构进行了表征。用MTT方法评价了它们在体外对HepG-2,A549-1和231-2 3种癌细胞株的体外生长抑制活性。结果表明,所合成的8个新化合物均具有潜在的体外抑制癌细胞生长活性,其中3-N-三氟乙酰基-2-(4-溴苯基)-5-(4-氟苯基)-1,3,4-噁唑啉、3-N-三氟乙酰基-2-(4-氯苯基)-5-(4-氟苯基)-1,3,4-噁唑啉活性最强。

Abstract：The arylcarboxylic acid hydrazides were prepared by esterification and hydrazinolysis of corresponding aromatic carboxylic acids. Arylcarboxylic acid hydrazides reacted witharomatic formaldehydes to give arylcarboxylic acid hydrazone and cyclodehydration of arylcarboxylic acid hydrazones with trifluoroacetic anhydride to afford 3-trifluoroacetyl-2,5-disubsti- tuted-1,3,4-oxadiazolines. The structures of target compounds were confirmed by elementary analyses, IR, LHNMR, UCNMR, and MS spectra. The in vitro anticancer activity against the threecancer celllines of HepG-2 ,A549-1 and 231-2 was evaluated. The bioactive assay indicated that 3-N-trifluoroacetyl-2-（4- bromophenyl ） -5-（ 4-fluorophenyl ） -1, 3,4-oxadiazoline and 3-N- trifluoroacetyl-2-（ 4-clorophenyl ）-5-（ 4-fluorophenyl ）- 1,3,4-oxadiazoline exhibited a significant anticancer activity.