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  

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

作　　者：石玉军[1,2] 方源[1] 李阳[1] 陈佳[2] 李刚[3] 汪清民[3] 戴红[2,3] 

机构地区：[1]江苏科技大学环境与化学工程学院,镇江212003 [2]南通大学化学化工学院,南通226019 [3]南开大学元素有机化学国家重点实验室,天津300071

出　　处：《高等学校化学学报》2017年第3期421-428,共8页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:21372135);元素有机化学国家重点实验室开放基金(批准号:201412)资助~~

摘　　要：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.In order noacrylates bearing to find novel cyanoacrylate derivatives with potent biological activities, fourteen new cya- 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 re- duction, chlorination, condensation, and hydrazine cleavage. The structures of target compounds 7 were con- firmed 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 in- hibitory activities against HepG2 cells with the IC50values of 3.2 and 10. 1 μmol/L, respectively.

关 键 词：异噁唑 氰基丙烯酸酯 生物活性 

分 类 号：O626[理学—有机化学]