303150-34-7

Basic information

• Product Name: 3-[(2,4-DICHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-AMINE
• Synonyms: 3-[(2,4-DICHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-AMINE;3-[(2,4-dichlorobenzyl)sulfanyl]-1H-1,2,4-triazol-5-ylamine;3-[(2,4-dichlorophenyl)methylsulfanyl]-1H-1,2,4-triazol-5-amine
• CAS NO: 303150-34-7
• Molecular Formula: C₉H₈Cl₂N₄S
• Molecular Weight: 275.16
• Mol File: 303150-34-7.mol

Chemical Properties

• Melting Point: 156-158°C
• Appearance: /
• CAS DataBase Reference: 3-[(2,4-DICHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2,4-DICHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-AMINE(303150-34-7)
• EPA Substance Registry System: 3-[(2,4-DICHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-AMINE(303150-34-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 303150-34-7(Hazardous Substances Data)

Upstream product

• 94-99-5 2,4-Dichlorobenzyl chloride 
• 16691-43-3 5-amino-3-mercapto-4H-[1,2,4]triazole 
• 20443-99-6 2,4-dichlorobenzyl bromide 
• 118025-46-0 3-amino-1H-1,2,4-triazole-5-thiol 
• 16691-43-3 3-amino-5-thioxo-1,2,4-triazole 

Downstream Products

• 341936-97-8 3⁽⁵⁾-acetylamino-5⁽³⁾-(2,4-dichlorobenzylthio)-1,2,4-triazole 
• 349142-05-8 1-acetyl-3⁽⁵⁾-acetylamino-5⁽³⁾-(2,4-dichlorobenzylthio)-1,2,4-triazole 

Relevant articles and documents

Structure based designing of triazolopyrimidone-based reversible inhibitors for kinases involved in NSCLC

Secondary acquired mutant EGFR (L858R-T790M)overexpressed NSCLC forms one of the prevalent form of resistant NSCLC. Another subset of resistant NSCLC includes amplified cMET in mutant EGFR derived tumours. Thus, in continuation to our previous work on the

Rickettsia prowazekii methionine aminopeptidase as a promising target for the development of antibacterial agents

Methionine aminopeptidase (MetAP) is a class of ubiquitous enzymes essential for the survival of numerous bacterial species. These enzymes are responsible for the cleavage of N-terminal formyl-methionine initiators from nascent proteins to initiate post-translational modifications that are often essential to proper protein function. Thus, inhibition of MetAP activity has been implicated as a novel antibacterial target. We tested this idea in the present study by targeting the MetAP enzyme in the obligate intracellular pathogen Rickettsia prowazekii. We first identified potent RpMetAP inhibitory species by employing an in vitro enzymatic activity assay. The molecular docking program AutoDock was then utilized to compare published crystal structures of inhibited MetAP species to docked poses of RpMetAP. Based on these in silico and in vitro screens, a subset of 17 compounds was tested for inhibition of R. prowazekii growth in a pulmonary vascular endothelial cell (EC) culture infection model system. All compounds were tested over concentration ranges that were determined to be non-toxic to the ECs and 8 of the 17 compounds displayed substantial inhibition of R. prowazekii growth. These data highlight the therapeutic potential for inhibiting RpMetAP as a novel antimicrobial strategy and set the stage for future studies in pre-clinical animal models of infection.

Discovery of inhibitors of Burkholderia pseudomallei methionine aminopeptidase with antibacterial activity

Evaluation of a series of MetAP inhibitors in an in vitro enzyme activity assay led to the first identification of potent molecules that show significant growth inhibition against Burkholderia pseudomallei. Nitroxoline analogues show excellent inhibition potency in the BpMetAP1 enzyme activity assay with the lowest IC50 of 30 nM and inhibit the growth of B. pseudomallei and B. thailandensis at concentrations ≥31 μM.

Synthesis of novel derivatives of 3(5)-alkylsulfonyl-1,2,4-triazoles

The feasibility of preparing novel 1,2,4-triazole derivatives bearing alkylsulfonyl and other functional groups on the ring carbon atom has been demonstrated. The syntheses are carried out via transformation of the amino group of 3(5)-alkylsulfonyl-5(3)-amino-1,2,4-triazoles into other functional groups.