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.

Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors

“…[18] Recently, flavonoids which include gallocatechin and quercetin and their derivatives have also been investigated against Helicobacter pylori's urease. [19,20] Various triazoles [21,22] and thiosemicarbazide Schiff bases have also been reported as urease inhibitors. [23][24][25] Heavy metal Schiff base derivatives proved to be toxic in humans.…”

Design, synthesis, and urease inhibition studies of some 1,3,4-oxadiazoles and 1,2,4-triazoles derived from mandelic acid

“…Among these, 1,3,4-oxadiazoles and 1,2,4-triazoles exhibit numerous biological activities such as antimicrobial [1][2][3] , anticonvulsant 4 , anti-human immunodeficiency virus (HIV) 5 , anticancer 6,7 , and urease inhibition 8,9 . Oxadiazoles and triazoles have been regarded as structural type inhibitors of urease 10 .…”

4-Ethoxybenzohydrazide

“…They have been employed as synthetic precursors for a number of hetero-cyclic compounds such as oxadiazoles, triazoles and thiadiazoles (Zia et al, 2012;Syed et al, 2011;Akhtar et al, 2010;Akhtar, Hameed, Al-Masoudi et al, 2008;Akhtar, Hameed, Khan et al, 2008;Khan, Akhtar et al , 2010;Khan, Hameed et al , 2010;Serwar et al, 2009;Zahid et al, 2009). The title compound (1) was synthesized as an intermediate for its subsequent conversion to 1,2,4-triazoles and 1,3,4-thiadiazoles in order to explore their potential as antibacterial or antifungal agents or urease inhibitors.…”