Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1- c][1,2,4]triazolo[3,4- f][1,2,4]triazines

Islam H El Azab; Nadia A A Elkanzi

doi:10.3390/molecules25061339

Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1- c][1,2,4]triazolo[3,4- f][1,2,4]triazines

Molecules. 2020 Mar 15;25(6):1339. doi: 10.3390/molecules25061339.

Authors

Islam H El Azab^{1

2}, Nadia A A Elkanzi^{2

3}

Affiliations

¹ Chemistry Department, Faculty of Science, Taif University, Al-Haweiah, P.O. Box 888, Taif 21974, Saudi Arabia.
² On leave from Chemistry Department, Faculty of Science, Aswan University, Aswan P.O. Box 81528, Egypt.
³ Chemistry Department, College of Science, Jouf University, P.O. Box 2014, Sakaka, Saudi Arabia.

Abstract

A series of 34 new pyrimido[2,1-c][1,2,4]triazine-3,4-diones were synthesized and fully characterized using IR, NMR, MS, and microanalytical analysis. In vitro investigation of 12 compounds of this series revealed promising antimicrobial activity of the conjugates 15a and 15f-j that were tagged with electron-withdrawing groups, with sensitivities ranging from 77% to as high as 100% of the positive control. The investigation of antimicrobial activity included Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6535, Pseudomonas aeruginosa ATCC 27853, and Escherichia coli ATCC 8739 (EC), and fungal strains Candida albicans ATCC 10231 and Aspergillus brasiliensis ATCC 16404.

Keywords: 1,2,4-triazine; 1,2,4-triazole; Mannich reaction; N-heterocycles; antimicrobial activity; pyrimidine.

MeSH terms

Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / pharmacology*
Bacteria / drug effects
Fungi / drug effects
Microbial Sensitivity Tests / methods
Triazines / chemical synthesis*
Triazines / pharmacology*
Triazoles / chemical synthesis*
Triazoles / pharmacology*

Substances

Anti-Infective Agents
Triazines
Triazoles