title: Syntheses, urease inhibition, and antimicrobial studies of some chiral 3-substituted-4-amino-5-thioxo-1H,4H-1,2,4-triazoles.
abstract: 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 IC(50) values ranging from 22.0 +/- 0.5 to 43.8 +/- 0.3 microM. Compound 5b was found to be the most active, exhibiting IC(50) = 22.0 +/- 0.5 microM comparable to the standard, thiourea (IC(50) = 21.0 +/- 0.1 microM). 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.
authors.affiliation: Department of Chemistry, Quaid-e-Azam University, Islamabad, 45320 Pakistan.
authors.forename: Tashfeen
authors.initials: T
authors.lastname: Akhtar
authors.forename: Shahid
authors.initials: S
authors.lastname: Hameed
authors.forename: Khalid Mohammed
authors.initials: KM
authors.lastname: Khan
authors.forename: Muhammad Iqbal
authors.initials: MI
authors.lastname: Choudhary
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013890:Thiourea / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014510:Urease / Q000037:antagonists & inhibitors*
chemical_list: D000890:Anti-Infective Agents; D004791:Enzyme Inhibitors; D014230:Triazoles; D014510:Urease; D013890:Thiourea