Medicinal Chemistry

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Kings College
University of Cambridge


Syntheses, Urease Inhibition, and Antimicrobial Studies of Some Chiral 3-Substituted-4-amino-5-thioxo-1H,4H-1,2,4-triazoles

Author(s): Tashfeen Akhtar, Shahid Hameed, Khalid Mohammed Khan and Muhammad Iqbal Choudhary

Affiliation: Department of Chemistry, Quaid-e-Azam University, Islamabad, 45320 Pakistan.


Chiral 3-substituted-4-amino-5-thioxo-1H,4H-1,2,4-triazoles (5a-i) were synthesized. The target molecules were prepared by cyclization of the corresponding dithiocarbazinic acids, obtained from hydrazides, in the presence of hydrazine hydrate. The chiral hydrazides were in turn synthesized form L-amino acids. The structures of all the compounds were confirmed by modern spectroscopic techniques and purity ascertained by elemental analysis. The synthesized compounds 5a-i were evaluated for urease inhibition and found to exhibit varying degrees of urease inhibition activity showing IC50 values ranging from 22.0 ± 0.5 to 43.8 ± 0.3 μM. Compound 5b was found to be the most active, exhibiting IC50 = 22.0 ± 0.5 μM comparable to the standard, thiourea (IC50 = 21.0 ± 0.1 μM). Triazoles 5a-i were also screened for their antimicrobial properties and promising antibacterial activities were observed against five pathogenic bacteria. However, all the compounds were devoid of any antifungal activity.

Keywords: Chiral triazoles, synthesis, antibacterial activity, urease inhibition

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Article Details

Page: [539 - 543]
Pages: 5
DOI: 10.2174/157340608786242025
Price: $58