Synthesis and Antimicrobial Screening of Novel 2-Thiopyrimidine Derivatives Bearing Pyrazole Moiety

Hekel, Ali J.; Awad, Samir M.; Nosseir, Ola; El-Shehry, Mohamed F.; El-Rashedy, Ahmed A.; Hammad, Sherif F.

doi:10.21608/ejchem.2024.323611.10511

	Synthesis and Antimicrobial Screening of Novel 2-Thiopyrimidine Derivatives Bearing Pyrazole Moiety
Egyptian Journal of Chemistry
Volume 68, Issue 5, May 2025, Page 645-652 PDF (1.09 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2024.323611.10511
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Authors
Ali J. Hekel¹; Samir M. Awad ²; Ola Nosseir¹; Mohamed F. El-Shehry³; Ahmed A. El-Rashedy ⁴; Sherif F. Hammad¹^{, 5}
¹Pharmaceutical Chemistry Department, Faculty of pharmacy, Helwan University, Egypt
²Pharmaceutical Organic Chemistry Department, Faculty of pharmacy, Helwan University, Egypt
³Pesticides Chemistry Department, National Research Centre, Dokki, Giza, 12622 Egypt
⁴Natural and Microbial Products Department, National Research Center, Egypt
⁵Pharm D Program, Egypt-Japan University of Science and Technology, New Borg-Arab City Alexandria 21934, Egypt
Abstract
2-Thiouracil-5-carbonitrile derivatives 2a,b were used as starting material for synthesis of the chloropyrimidines 3a,b , and then reacted with thiourea to give the pyrimidine dithione derivatives 4a,b. The chloropyrimidines 3a,b were then methylated with methyl iodide to yield the methyl mercaptopyrimidines 5a,b. Following that , 4-mercapto-2-thiopyrimidine derivatives 6a,b were synthesized via a reaction between methyl mercaptopyrimidines 5a,b and thioura. Moreover, from 6a,b a series of thiopyrimidines derivatives 7a,b and 8a,b were synthesized. All compounds were screened against select microorganisms to assess their antimicrobial activity. Compounds 4b, 6a, and 8b showed the highest antibacterial activity among the synthesized derivatives . As a result, the three compounds were selected for a molecular docking study against the bacterial dihydropteroate synthase enzyme to which they revealed a good binding affinity.
Keywords
Thiopyrimidine-5-carbonitrile; antimicrobial; dihydropteroate synthase; molecular docking


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