152473-68-2

Usage

InChI:InChI=1/C10H13N3OS/c1-7-3-5-9(6-4-7)11-10(15)13-12-8(2)14/h3-6H,1-2H3,(H,12,14)(H2,11,13,15)

Upstream product

• 1068-57-1 acetic acid hydrazide 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 75-36-5 acetyl chloride 
• 13278-67-6 4-(4-methylphenyl)-3-thiosemicarbazide 

Downstream Products

• 149747-23-9 5-methyl-4-p-tolyl-4H-[1,2,4]triazole-3-thiol 
• 23585-94-6 5-methyl-N-p-tolyl-1,3,4-oxadiazol-2-amine 
• 149747-23-9 5-methyl-4-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 493026-69-0 2-(5-methyl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-N-(2-nitro-phenyl)-acetamide 

Relevant academic research and scientific papers

Antimicrobial and Physicochemical Characterizations of Thiosemicarbazide and S-Triazole Derivatives

Two series of thiosemicarbazide derivatives and three series of s-triazole derivatives have been synthesized. All of these compounds were tested for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. Among tested thiosemicarbazide derivatives, the best bioactivity was detected for two 1-formylthiosemicarbazides with 3-/4-tolyl substitution (1 l, 1 m) (MICs range between 31.25 and 250 μg/mL). All tested s-triazole derivatives exhibited lower antibacterial activity than their acyclic precursors.

Desulfurization strategy in the construction of azoles possessing additional nitrogen, oxygen or sulfur using a copper(I) catalyst

A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper( I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable nucleophiles. For aminotetrazoles and triazoles an excellent regioselectivity has been achieved through proper tuning of the pKa values of the parent amines attached to unsymmetrical thioureas. The method represents an autocatalytic process in which copper( I) iodide gets converted to copper(II) sulfide which in turn transforms to active copper(II) oxide that effectively carries forward the catalytic cycle. The fate of the copper catalyst has also been studied using scanning electron microscopic (SEM) and energy-dispersive X-ray spectroscopic (EDS) analyses which give an insight into the mechanism for this catalytic process.

Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors

A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization.