新型含N杂环化合物的合成、生物活性及量化计算
发布时间：2018-09-10 19:25
【摘要】：含N杂环衍生物由于具有广谱的生物活性,其合成与性质研究成为化学和生物工作者研究的热点。为了筛选可能具有抑菌潜力的新型含N杂环衍生物,本文设计合成了50个1,2,4-三唑和4个异VA唑化合物,并对它们的性质进行了研究。5-取代-4-氨基-1,2,4-三唑-3-硫酮希夫碱的合成：以甲酸、乙酸、丙酸、正丁酸、苯乙酸、4-吡啶甲酸、4-甲基苯甲酸、2-甲氧基苯甲酸为原料合成中间体5-取代-4-氨基-1,2,4-三唑-3-硫酮,再分别与2-氯-6-氟苯甲醛、3-苯氧基苯甲醛、4-吡啶甲醛、2,3,6-三甲基-4-甲氧基苯甲醛、4-(1H咪唑)苯甲醛、5-溴-2-羟基-3-甲氧基苯甲醛、呋喃甲醛、4-甲氧基苯乙酮缩合,生成50个1,2,4-三唑希夫碱化合物,48个未见文献报道。并且得到5个化合物(Ⅱ13、Ⅱ14、Ⅱ34、Ⅱ49、Ⅱ50)的晶体结构。所有合成的目标化合物通过熔点、元素分析、红外、核磁表征。3-(2-氯-6-氟苯基)-5-芳基-4-芳酰基异VA唑的合成：以2-氯-6-氟苯甲醛为原料,先合成中间体2-氯-6-氟苯甲醛肟氯,再分别与查尔酮、2-氟取代查尔酮、3-氟取代查尔酮和4-氟取代查尔酮发生1,3-偶极加成反应,生成了4个未见文献报道的异嗯唑衍生物。得到1个异VA唑(3a)化合物的单晶。它们的结构通过熔点、元素分析、红外、核磁表征。以化合物Ⅱ49为例,采用DFT/B3LYP和HF两种方法、6-311G+(d,p)和6-311G两种基组对化合物Ⅱ49进行了结构优化和频率计算,所有计算频率都没有虚频。以DFT、 HF两种方法的结构参数、FI-IR.核磁与实验值作对比。得出结论：DFT/B3LYP方法更接近实验值,6-311G+(d,p)和6-311G两组基组计算结果差别不是特别明显。参考化合物Ⅱ49计算得出的结论,用DFT/B3LYP方法、中等大小的基组6-31G(d)对化合物Ⅱ13、Ⅱ14、Ⅱ34、Ⅱ50进行结构优化和频率计算,得到最优构型。并计算了化合物的自然电荷和前沿轨道能量。化合物3a用DFT/B3 L YP/6-31 G+(d,P)方法进行结构优化和频率计算,并计算了它的FI-IR、自然电荷和前沿轨道能量。采用室内平皿法测定了化合物Ⅱ1-32、Ⅱ49-50、3a-d对烟草赤星病、马铃薯干腐病、小麦赤霉病、西瓜枯萎病4种植物病原菌的室内离体抑菌活性；同种方法测定了化合物Ⅱ33-48在浓度为50 ug·mL-1时对小麦赤霉病、番茄早疫病、辣椒疫霉病、黄瓜枯萎病、花生褐斑病、苹果轮纹病6种植物病原菌的室内离体抑菌活性。测试结果显示合成的部分化合物对所测菌种具有显著的抑菌作用。采用K-B纸片法,定性的测试了化合物Ⅱ1-50和3a-d在浓度为100 ug·mL-1时对枯草芽孢杆菌、金黄色葡萄球菌、大肠杆菌3种细菌的抑菌活性。真菌活性测试和细菌活性测试均表明当引入3-苯氧基苯甲醛,三唑环上5-位取代为无取代时会增强化合物的活性。
[Abstract]:The synthesis and properties of N-containing heterocyclic derivatives have become the focus of chemical and biological research because of their broad-spectrum biological activity. In order to screen novel N-containing heterocyclic derivatives with potential bacteriostatic potential, 50 compounds of 1h2h4- triazole and 4 iso-VA azoles were designed and synthesized. Their properties have also been studied. The synthesis of Schiff bases of 5- substituted -4-amino-1-aniline, 4-triazole-3-thione: in formic acid, acetic acid, propionic acid, butyric acid, Synthesis of intermediate 5- substituted -4-amino-1-triazole-3-thione from 4-pyridine-4-methylbenzoic acid and 2-methoxy benzoic acid And then condensed with 2-chloro-6-fluorobenzaldehyde and 4-pyridine formaldehyde, respectively. The condensation of 4- (1H-imidazole) benzaldehyde with 5-bromo-2-hydroxy-3-methoxy benzaldehyde, furan formaldehyde with 4-methoxy acetophenone, Fifty compounds of 1, 2 and 4-triazole Schiff base were synthesized, and 48 compounds have not been reported in the literature. The crystal structures of five compounds (鈪，
本文编号：2235392
[Abstract]:The synthesis and properties of N-containing heterocyclic derivatives have become the focus of chemical and biological research because of their broad-spectrum biological activity. In order to screen novel N-containing heterocyclic derivatives with potential bacteriostatic potential, 50 compounds of 1h2h4- triazole and 4 iso-VA azoles were designed and synthesized. Their properties have also been studied. The synthesis of Schiff bases of 5- substituted -4-amino-1-aniline, 4-triazole-3-thione: in formic acid, acetic acid, propionic acid, butyric acid, Synthesis of intermediate 5- substituted -4-amino-1-triazole-3-thione from 4-pyridine-4-methylbenzoic acid and 2-methoxy benzoic acid And then condensed with 2-chloro-6-fluorobenzaldehyde and 4-pyridine formaldehyde, respectively. The condensation of 4- (1H-imidazole) benzaldehyde with 5-bromo-2-hydroxy-3-methoxy benzaldehyde, furan formaldehyde with 4-methoxy acetophenone, Fifty compounds of 1, 2 and 4-triazole Schiff base were synthesized, and 48 compounds have not been reported in the literature. The crystal structures of five compounds (鈪，
本文编号：2235392
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