Design, Synthesis, and Structure–Activity Relationships of Novel N-Substituted-5-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-2-amine for Their Anti-HIV and Antibacterial Activities

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]tri...

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Published in:Russian journal of bioorganic chemistry 2022-12, Vol.48 (6), p.1221-1229
Main Authors: Alagarsamy, V., Narendhar, B., Chitra, K., Sriram, D., Sarvanan, G., Solomon, V. Raja
Format: Article
Language:English
Subjects:
Amines
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Dilution
E coli
Life Sciences
Optimization
Organic Chemistry
Substitution reactions
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Summary: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.
ISSN:1068-1620
1608-330X
DOI:10.1134/S106816202206005X