新型含5-芳基异噁唑结构的氰基丙烯酸酯类化合物的合成及生物活性

通过5-取代苯基异噁唑-3-甲基胺与2-氰基-3,3-二甲硫基丙烯酸取代酯的缩合反应,合成了一系列含5-取代苯基异噁唑环结构的氰基丙烯酸酯类衍生物,并采用核磁共振波谱和元素分析对化合物的结构进行了表征.初步的生物活性测试结果表明,部分化合物显示出较好的除草活性,在1500 g/ha剂量下,化合物7h,7i和7m对芥菜的茎叶处理抑制率分别为90%,40%和100%;化合物7m和7n对繁缕的茎叶处理抑制率分别为100%和80%;化合物7m和7n对小藜的茎叶处理抑制率分别为100%和85%.此外,化合物7b和7c还表现出良好的抗肿瘤活性,其对HepG2细胞的IC50值分别为3.2和10.1μmol/L.

Synthesis and Biological Activities of Novel Cyanoacrylate Derivatives Carrying 5-Arylisoxazole Group

In order to find novel cyanoacrylate derivatives with potent biological activities,fourteen new cyanoacrylates bearing a 5-arylisoxazole moiety were synthesized by multistep synthetic procedures with two key intermediates 5 and 6.The intermediate 5 was synthesized from methyl 5-arylisoxazolyl-3-carboxylate via reduction,chlorination,condensation,and hydrazine cleavage.The structures of target compounds 7 were confirmed by 1H NMR,13C NMR and elemental analysis.The bioassay data showed that some target compounds exhibited good herbicidal activities at the dosage of 1500 g/ha.In postemergence treatment,compounds 7h,7i,and 7m had 90％,40％,and 100％ herbicidal activity against Brassica juncea at 1500 g/ha,compounds 7m and 7n showed 100％ and 80％ herbicidal activity against Stellaria media at 1500 g/ha,compounds 7m and 7n displayed 100％ and 85％ inhibitory rates against Chenopodium serotinum L.at 1500 g/ha.In addition,some of the title compounds had satisfactory anti-tumor activities.Compounds 7b and 7c showed wonderful inhibitory activities against HepG2 cells with the IC50values of 3.2 and 10.1 μmol/L,respectively.