Synthesis of new 4,5-substituted 4H-1,2,4-triazole-3-thiols and their sulfanyl derivatives

Kaldrikyan, M. A.; Minasyan, N. S.; Melik-Ogandzhanyan, R. G.

doi:10.1134/s1070363215030160

Cited by 4 publications

(1 citation statement)

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“…(R 1 = 4-CH 3 OPh); 4-methoxybenzohydrazide 16g and benzyl isothiocyanate were refluxed in EtOH for 5 h. Yield: 91% (white solid); 194–196 °C (lit . 202–203 °C).…”

Section: Methodsmentioning

confidence: 99%

Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-d-ribofuranose 2′-Oxidase

et al. 2019

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We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure–activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H37Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 μM, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-β-d-ribofuranose 2′-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.

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“…(R 1 = 4-CH 3 OPh); 4-methoxybenzohydrazide 16g and benzyl isothiocyanate were refluxed in EtOH for 5 h. Yield: 91% (white solid); 194–196 °C (lit . 202–203 °C).…”

Section: Methodsmentioning

confidence: 99%