新型含N雜環(huán)化合物的合成、生物活性及量化計算
發(fā)布時間：2018-09-10 19:25
【摘要】：含N雜環(huán)衍生物由于具有廣譜的生物活性,其合成與性質(zhì)研究成為化學(xué)和生物工作者研究的熱點。為了篩選可能具有抑菌潛力的新型含N雜環(huán)衍生物,本文設(shè)計合成了50個1,2,4-三唑和4個異VA唑化合物,并對它們的性質(zhì)進(jìn)行了研究。5-取代-4-氨基-1,2,4-三唑-3-硫酮希夫堿的合成：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-甲氧基苯甲酸為原料合成中間體5-取代-4-氨基-1,2,4-三唑-3-硫酮,再分別與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-羥基-3-甲氧基苯甲醛、呋喃甲醛、4-甲氧基苯乙酮縮合,生成50個1,2,4-三唑希夫堿化合物,48個未見文獻(xiàn)報道。并且得到5個化合物(Ⅱ13、Ⅱ14、Ⅱ34、Ⅱ49、Ⅱ50)的晶體結(jié)構(gòu)。所有合成的目標(biāo)化合物通過熔點、元素分析、紅外、核磁表征。3-(2-氯-6-氟苯基)-5-芳基-4-芳酰基異VA唑的合成：以2-氯-6-氟苯甲醛為原料,先合成中間體2-氯-6-氟苯甲醛肟氯,再分別與查爾酮、2-氟取代查爾酮、3-氟取代查爾酮和4-氟取代查爾酮發(fā)生1,3-偶極加成反應(yīng),生成了4個未見文獻(xiàn)報道的異嗯唑衍生物。得到1個異VA唑(3a)化合物的單晶。它們的結(jié)構(gòu)通過熔點、元素分析、紅外、核磁表征。以化合物Ⅱ49為例,采用DFT/B3LYP和HF兩種方法、6-311G+(d,p)和6-311G兩種基組對化合物Ⅱ49進(jìn)行了結(jié)構(gòu)優(yōu)化和頻率計算,所有計算頻率都沒有虛頻。以DFT、 HF兩種方法的結(jié)構(gòu)參數(shù)、FI-IR.核磁與實驗值作對比。得出結(jié)論：DFT/B3LYP方法更接近實驗值,6-311G+(d,p)和6-311G兩組基組計算結(jié)果差別不是特別明顯。參考化合物Ⅱ49計算得出的結(jié)論,用DFT/B3LYP方法、中等大小的基組6-31G(d)對化合物Ⅱ13、Ⅱ14、Ⅱ34、Ⅱ50進(jìn)行結(jié)構(gòu)優(yōu)化和頻率計算,得到最優(yōu)構(gòu)型。并計算了化合物的自然電荷和前沿軌道能量�；衔�3a用DFT/B3 L YP/6-31 G+(d,P)方法進(jìn)行結(jié)構(gòu)優(yōu)化和頻率計算,并計算了它的FI-IR、自然電荷和前沿軌道能量。采用室內(nèi)平皿法測定了化合物Ⅱ1-32、Ⅱ49-50、3a-d對煙草赤星病、馬鈴薯干腐病、小麥赤霉病、西瓜枯萎病4種植物病原菌的室內(nèi)離體抑菌活性；同種方法測定了化合物Ⅱ33-48在濃度為50 ug·mL-1時對小麥赤霉病、番茄早疫病、辣椒疫霉病、黃瓜枯萎病、花生褐斑病、蘋果輪紋病6種植物病原菌的室內(nèi)離體抑菌活性。測試結(jié)果顯示合成的部分化合物對所測菌種具有顯著的抑菌作用。采用K-B紙片法,定性的測試了化合物Ⅱ1-50和3a-d在濃度為100 ug·mL-1時對枯草芽孢桿菌、金黃色葡萄球菌、大腸桿菌3種細(xì)菌的抑菌活性。真菌活性測試和細(xì)菌活性測試均表明當(dāng)引入3-苯氧基苯甲醛,三唑環(huán)上5-位取代為無取代時會增強化合物的活性。
[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，
本文編號：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，
本文編號：2235392
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