Abstract

A new series of N-substituted-5-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-2-amine (XIa–o) were synthesized by the nucleophilic substitution reaction of 4-(2-(methylthio)-5-phenyl-[1,2,4]triazolo quinazoline (X) with different aryl amines. The starting material 2-(methylthio)-5-phenyl-[1,2,4]triazolo quinazoline (X) was synthesized from anthranilic acid. All synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against selective gram-positive and gram-negative bacteria by agar dilution method. Among the series, compound N-(4-nitrophenyl)-5-phenyl-[1,2,4]triazolo[1,5-c]-quinazolin-2-amine (IXi) and N-(4-chlorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-c]-quinazolin-2-amine (IXk) showed the most potent activity against E. coli, P. aeruginosa and S. epidermidis with the MIC of 3 µg/mL. The compound (IXi) exhibited the antitubercular activity at 6.25 µg/mL and anti-HIV activity at 7.15 µg/mL, respectively, against HIV1 and HIV2. It can be offered the potential for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated triazolo quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities.

中文翻译：

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新型 N-取代-5-苯基-[1,2,4]三唑并[1,5-c]喹唑啉-2-胺的抗 HIV 和抗菌活性的设计、合成和构效关系

摘要

由4- ( 2- _ _ _ (甲硫基)-5-苯基-[1,2,4]三唑并喹唑啉( X )与不同的芳基胺。起始原料2-(甲硫基)-5-苯基-[1,2,4]三唑并喹唑啉( X )以邻氨基苯甲酸为原料合成，采用琼脂稀释法筛选了所有合成化合物的抗结核、抗HIV和对选择性革兰氏阳性和革兰氏阴性菌的抗菌活性，其中化合物N- (4-nitrophenyl)-5 -苯基-[1,2,4]三唑并[1,5 - c ]-喹唑啉-2-胺（IXi) 和N- (4-氯苯基)-5-苯基-[1,2,4]三唑并[1,5 - c ]-quinazolin-2-amine ( IXk ) 对大肠杆菌、P. MIC 为 3 µg/mL 的绿脓杆菌和表皮葡萄球菌。化合物 ( IXi ) 对 HIV1 和 HIV2 分别表现出 6.25 µg/mL 的抗结核活性和 7.15 µg/mL 的抗 HIV 活性。它可以提供进一步优化和开发新的抗结核和抗 HIV 药物的潜力。从这项研究中获得的结果证实，合成和生物学评估的三唑并喹唑啉具有良好的抗菌、抗结核和抗 HIV 活性。