124980-06-9

Basic information

• Product Name: 4-AMINO-5-(3-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: BUTTPARK 25\07-94;4-AMINO-5-(3-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL;AKOS TOT-0027;A4390/0187369;ZINC02635301
• CAS NO: 124980-06-9
• Molecular Formula: C₈H₇FN₄S
• Molecular Weight: 210.23
• Mol File: 124980-06-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-AMINO-5-(3-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(3-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(124980-06-9)
• EPA Substance Registry System: 4-AMINO-5-(3-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(124980-06-9)

Safety Data

• Hazardous Substances Data: 124980-06-9(Hazardous Substances Data)

Upstream product

• 455-38-9 3-fluorobenzoic acid 
• 455-68-5 methyl 3-fluorobenzoate 
• 75-15-0 carbon disulfide 
• 499-55-8 3-fluoro-benzoic acid hydrazide 
• 1711-07-5 3-fluorobenzoyl chloride 
• 166093-17-0 C₈H₆FN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 2231-57-4 Thiocarbohydrazide 
• 451-02-5 ethyl 3-fluorobenzoate 

Downstream Products

• 1034738-22-1 6-(1-adamantyl)-3-(3-fluorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1293362-48-7 methyl 3-(3-(3-fluorophenyl)-5-thioxo-1H-1,2,4-triazol-4-ylimino)cholanate 

Relevant articles and documents

Synthesis, characterization and antimicrobial evaluation of some new schiff, mannich and acetylenic mannich bases incorporating a 1,2,4-triazole nucleus

A series of Schiff and Mannich bases derived from 4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione were synthesized. The alkylation of 4-phenyl-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione with propargyl bromide afforded the corresponding thiopropargylated derivative which upon treatment with the appropriate secondary amines in the presence of CuCl2 furnished the desired acetylenic Mannich bases. The synthesized compounds were characterized on the basis of their spectral (IR, 1H- and 13C-NMR) data and evaluated for their biological activities. Some of the compounds were found to exhibit significant antimicrobial activity.

1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases

Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.

METHODS FOR TREATING VIRAL INFECTION

A method effective in treating a viral infection involves administering a therapeutically effective amount of at least one compound capable of inhibiting expression of at least a portion of a virus genome containing an internal ribosomal entry site, or a pharmaceutically acceptable salt thereof. The compound has an azole moiety comprising a five member heterocyclic ring containing at least one nitrogen atom, a hydrophobic moiety bonded to the heterocyclic ring of the azole, and a donor / acceptor moiety bonded to the heterocyclic ring having at least one of hydrogen bond donor and a hydrogen bond acceptor.