新型吡唑酰腙类化合物的合成及其生物活性  

Synthesis and Biological Activities of Novel Acylhydrazone Compounds Containing Pyrazole Group

作　　者：谢艳[1] 王玉申 龚华玉[1] 吴小琼[3] 王晓斌[1] 肖维[1] 汪华[4] 薛伟[1] XIE Yan WANG Yu-shen GONG Hua-yu WU Xiao-qlong WANG Xiao-bin XIAO Wei WANG Hua XUE Wei(State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Guizhou University, Guiyang 550025, China Shandong Changyi Jiayuanhuagong Chemical Ltd. , Changyi 261303, China Vocational and Technical College of Anshun, Anshun 561000, China Institute of Plant Protection and Soil Fertilizer, Hubei Academy of Agricutural Science, Wuhan 430064, China)

机构地区：[1]贵州大学绿色农药与农业生物工程国家重点实验室培育基地,贵州贵阳550025 [2]山东昌邑家园化工有限公司,山东昌邑261303 [3]安顺职业技术学院,贵州安顺561000 [4]湖北省农业科学院植保土肥所,湖北武汉430064

出　　处：《合成化学》2016年第10期837-842,共6页Chinese Journal of Synthetic Chemistry

基　　金：贵州省优秀青年科技人才培养专项(201535);公益性行业农业科研专项(20150311-8)

摘　　要：以取代肼和取代乙酰乙酸乙酯为起始原料,依次经闭环、氯酰化、氧化、酯化及取代反应制得1,3-取代-5-氯-4-吡唑甲酰肼(7a,7d,7g和7j);7分别与取代呋喃或噻吩甲醛经加成反应合成了12个新型的吡唑酰腙类化合物(9a^9l),其结构经1H NMR,13C NMR,IR和元素分析表征。初步的生物活性测试结果表明:在500μg·m L-1浓度下,部分化合物对烟草花叶病毒(TMV)具有一定的抑制活性,其中1-苯基-3-三氟甲基-5-氯-4-(2-噻吩)-腙基羰基吡唑(9k)的治疗活性、保护活性和钝化活性分别为63.6%,85.7%和93.1%,与对照药宁南霉素(65.9%,86.4%和97.8%)相当;在50μg·m L-1浓度下,部分化合物表现出一定的抑菌活性,其中1,3-二甲基-5-氯-4-(2-噻吩)-腙基羰基吡唑(9b)与1-甲基3-三氟甲基-5-氯-4-(2-噻吩)-腙基羰基吡唑(9e)对小麦赤霉病菌(Gibberella zeae)的抑制率分别为42.5%和46.8%。1,3-Disubstituted 5-chloro-4-pyrazole formyl hydrazines（7a, 7d, 7g and 7j） were prepared by ring-closing, chlorine acylation, oxidation, esterification and substitution addition reaction, using substituted hydrazine and substituted ethyl acetoacetate as starting materials. Twelve novel pyrazole acylhydrazone compounds（9a-91） were synthesized by addition reaction of 7 with furan or thiophene, respectively. The structures were characterized by 1n NMR, 13C NMR, IR and elemental analysis. The bioassay results showed that some title compounds showed certain antiviral activity against tobacco mosaic virus （TMV） at a concentration of 500 μg·mL^-1. Particularly, the protection, treatment and passivation activities of 1-phenyl-3-trifluoromethyl-5-chloro-4-（2-thiophene）-hydrazone carbonyl pyrazole （9k） were 63.6% , 85.7% and 93.1%, respectively, slightly lower than the contrast agents Ning- nanmycin （65.9%, 86.4% and 97.8% ）. Part of the compounds showed certain antibacterial activities against G. zeae, inhibition ratio of 1,3-dimethy-5-chloro4- （2-thiophene）-hydrazone carbonyl pyrazole （9b） and 1 -methy-3-trifluoromethyl-5 -chloro-4- （ 2-thiophene ） -hydrazone carbonyl pyrazole （ 9e ） were 42.5% and 46.8% at 50 trg · mL-I, respectively.

关 键 词：肼 乙酰乙酸乙酯 吡唑 酰腙 合成 生物活性 

分 类 号：O621.3[理学—有机化学] O626[理学—化学]