13373-10-9

Usage

Uses

Used in Pharmaceutical Research:
4-AMINO-5-BENZYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE is used as a potential anti-cancer agent for its ability to inhibit the enzyme methylthioadenosine phosphorylase, which may contribute to the suppression of tumor growth and progression.
Used in Organic Synthesis:
4-AMINO-5-BENZYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE is used as a key intermediate in the synthesis of various organic compounds, leveraging its unique chemical structure and reactivity.
Used in Antimicrobial Applications:
4-AMINO-5-BENZYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE is used as an antimicrobial agent due to its potential to inhibit the growth of certain bacteria, making it a candidate for further research and development in the field of infectious diseases.
Used in Antifungal Applications:
4-AMINO-5-BENZYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE is used as an antifungal agent for its potential to combat fungal infections, offering a new avenue for treatment options in medical mycology.

Upstream product

• 87239-94-9 potassium-3-(phenylacetyl)dithiocarbazate 
• 103-82-2 phenylacetic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 23288-90-6 2-mercapto-5-benzyl-1,3,4-oxadiazole 
• 937-39-3 2-phenylacetylhydrazine 
• 75-15-0 carbon disulfide 
• 2231-57-4 Thiocarbohydrazide 
• 101-97-3 Ethyl 2-phenylethanoate 

Downstream Products

• 111828-12-7 (4-Amino-5-benzyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid methyl ester 
• 111827-92-0 N-(3-Benzyl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-acetamide 
• 708995-56-6 3-benzyl-6-(4-bromophenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 708292-90-4 3-benzyl-6-(3-bromophenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 898059-45-5 3-benzyl-6-(2-bromophenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 708997-85-7 3-benzyl-6-(1-naphthylmethyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1213786-79-8 3-benzyl-6-(1H-2-indolylmethyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 79074-69-4 3-Phenylmethyl-s-triazolo<3,4-b><1,3,4>thiadiazol-6(5H)-thione 
• 1092717-09-3 5-benzyl-4-[(2-hydroxybenzylidene)amino]-2,4-dihydro-4H-1,2,4-triazole-3-thione 

Relevant academic research and scientific papers

Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors

In an effort to develop new inhibitors of metallo-β-lactamases (MβLs), twenty-eight azolylthioacetamides were synthesized and assayed against MβLs. The obtained benzimidazolyl and benzioxazolyl substituted 1–19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20–28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2–4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group.

Synthesis, characterization, in vitro biological and computational evaluation of 5-benzyl-4-(benzylideneamino)-2H-1,2,4-triazole-3(4H)-thiones

Triazoles and their heterocyclic analogues are nitrogen-rich versatile pharmacophores easily synthesized and converted to a range of biologically relevant heterocycles. In this context, the present research reports the synthesis, characterization, in vitr

4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors

Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.

Synthesis, Antimicrobial, and Antioxidant Screening of Aryl Acetic Acid Incorporated 1,2,4-Triazolo-1,3,4-Thiadiazole Derivatives

Some novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives were synthesized from aryl acetic acids. All the synthesized derivatives were selected for the screening of antibacterial potential against Gram-positive bacteria [Staphylococcus aureus (MTCC 3160) and Micrococcus luteus (MTCC 1538)] and Gram-negative bacteria [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)] and antifungal potential against Aspergillus niger (MTCC 8652) and Candida albicans (MTCC 227), and free radical scavenging activity through 2,2-diphenyl-2-picrylhydrazyl hydrate method. The compounds TH-4, TH-13, and TH-19 were found to be more potent antimicrobial agents compared to standard drugs. The compounds TH-3, TH-9, and TH-18 also showed significant antimicrobial activity. The compound TH-13 showed antioxidant activity with IC50 value better than the standard compound. The structures of all the synthesized compounds were confirmed by Fourier transform infrared, 1H-NMR, liquid chromatography–mass spectrometry, and CHN analyzer.

Synthesis of Novel 1,2,4-Triazole-3-thione Derivatives as Influenza Neuraminidase Inhibitors

A series of 1,2,4-triazole-3-thione derivatives (6a–6t) were synthesized and evaluated against influenza viruses (H1N1) neuraminidase (NA) in vitro. Eighteen compounds exhibited inhibitory potency with IC50 values ranging from 14.68?±?0.49 to 39.85?±?4.23?μg/mL. Among them, compounds 6e and 6h showed significant inhibitory activity with IC50 values of 14.97?±?0.70 and 14.68?±?0.49?μg/mL, respectively. Structure activity relationships were established. Molecular docking studies were performed to understand the binding interaction between active compounds and NA.

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.

INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE

Compounds and salts thereof which are acyl-sulfonamides or certain carboxylic acids and which inhibit microbial growth or attenuate the virulence of pathogenic microorganisms and which inhibit UDP-galactopyranose mutase (UGM). Compounds of the invention include 2-aminothiazoles and triazolothiadiazines, particularly 3,6,7-substituted-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, and 2-amino and salts thereof. Methods for inhibiting growth or attenuating virulence of microbial pathogens including mycobacterium, for example, M. tuberculosis and M. smegmatis and Klebsiella, for example, Klebsiella pneumoniae. Methods for inhibiting eukaryotic human and animal pathogens, and fungi and nematodes in particular. Methods for treatment of infections by prokaryotic and eukaryotic pathogens employing compounds of the invention.

Synthesis and bioevaluation of Schiff and Mannich bases of isatin derivatives with 4-amino-5-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

Isatin (2,3-dioxindole) and its derivatives show a wide range of biological activities. In the present study, a series of Schiff and Mannich bases of isatin derivatives were prepared using 4-amino-5-benzyl-2,4-dihydro-3H- 1,2,4-triazole-3-thione. The stru

Synthesis and antihyperlipidemic activity of some novel 4-(substitutedamino)-5-substituted-3-mercapto-(4H)-1,2,4-triazoles

Hyperlipidemia is considered one of the key factors for cardiovascular diseases. Based on earlier work on a series of 5-alkyl-4-aryl-3-mercapto-(4H)-1, 2,4-triazoles, for further lead modification, a series of 4-(substituted)amino- 5-substituted-3-mercapto-(4H)-1,2,4-triazoles was designed. Target compounds were synthesized by the well known Hoggarth synthesis of substituted 1,2,4-triazoles. Synthesized compounds were screened for lipid lowering activity using the "Poloxamer 407 induced hyperlipidemia in rats" model at a dose of 100 mg/kg p. o. Compounds were found to alter serum lipid levels significantly. Most of the compounds significantly reduced serum cholesterol and triglyceride levels. Some of the compounds were found to reduce triglycerides and elevate high density lipoprotein (HDL) levels more than the standard drug atorvastatin (CAS 134523-03-8). Compounds with chloro substitution on aryl rings were found more active in reducing serum lipid levels than other substitutions. ECV ? Editio Cantor Verlag.

Studies on fused heterocyclic 3,6-disubstituted-1,2, 4-triazolo-1,3,4- thiadiazoles: Synthesis and biological evaluation

In this study, a series of 3,6-disubstituted-1,2, 4-triazolo-[3,4-b]-1,3,4- thiadiazoles (5a-t) were synthesized by condensing 4-amino-3-mercapto-(4H)-1,2, 4-triazoles (4a-c) with different aromatic or aroyl acids through one-pot reaction. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation actions. Some of the newly synthesized compounds showed very good anti-inflammatory activity with low GI toxicity and reduced lipid peroxidation. These compounds also showed interesting profile of analgesic activity in acetic acid-induced writhing test. The findings of the study indicate that the synthesized compounds have superior GI safety profile along with reduction in lipid peroxidation as compared to that of the standard. Springer Science+Business Media, LLC 2010.