4-甲基-1,2,3-噻二唑-5-甲酸芳酯的合成及生物活性
Synthesis and biological activity of 4-methyl-1,2,3-thiadiazole-5-carboxylates
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摘要: 为了寻找高效广谱的植物激活剂候选化合物,以三乙胺为缚酸剂,通过4-甲基-1,2,3-噻二唑-5-甲酰氯与酚类化合物在二氯甲烷中于室温下反应,制得一系列共20个4-甲基-1,2,3-噻二唑-5-甲酸芳酯化合物,其中9个化合物未见文献报道,所有化合物的结构均得到了核磁共振氢谱、红外光谱、高分辨质谱的表征和确认。选择化合物 2g 培养了单晶,利用X-射线单晶衍射确证了该类化合物的空间结构。杀菌活性测定结果表明:部分化合物在50 μ g/mL下具有显著的离体杀菌活性,其中化合物 2c,2n和2o 具有广谱的杀菌活性,其EC50值在3.46~23.30 μ g/mL之间。生物活性测定结果表明,部分化合物显示了较好的抗病毒活性,大部分化合物对烟草花叶病毒(TMV)具有较好的钝化效果, 2a,2c,2d,2e,2f,2g,2l,2o 具有较好的诱导烟草抗TMV的活性。Abstract: Heterocyclic compounds had various biological activities,in order to explore novel elicitors with a broad spectrum and highly systemic acquired resistance,a series of 4-methyl-1,2,3-thiadiazole-5-carboxylates were synthesized by using 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and substituted hydroxyl aromatic compounds as reactants.These reactions were conducted in dichloromethane at room temperature and using triethylamine as acid binding agent.All synthesized compounds including 9 new structures were confirmed by 1H NMR,IR and HRMS.Crystal structure of 2g was cultured and characterized by X-ray crystal diffraction method to validate the detailed chemical structure for this kind of compounds.Bioassay indicated that some compounds possessed obvious fungicidal activity at a concentration of 50 μ g/mL.Among these compounds, 2c,2n and 2o possessed a broad spectrum of fungicidal activity and EC50 value of these compounds ranged from 3.46 to 23.30 μ g/mL.Antivirus activity screening indicated that some compounds possessed good anti-TMV activity and most compounds displayed good inactivation activity against TMV.Moreover,compounds including 2a,2c,2d,2e,2f,2g,2l and 2o exhibited good systemic acquired resistance for tobacco against TMV as compared with positive control agents.
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