87239-95-0

Usage

InChI:InChI=1/C9H10N4S/c1-6-4-2-3-5-7(6)8-11-12-9(14)13(8)10/h2-5H,10H2,1H3,(H,12,14)

Upstream product

• 2503-66-4 5-o-tolyl-3H-[1,3,4]oxadiazole-2-thione 
• 75-15-0 carbon disulfide 
• 7658-80-2 2-methylbenzohydrazide 
• 85103-39-5 2-(2-methylbenzoyl)hydrazinecarbodithioic acid potassium salt 
• 118-90-1 ortho-methylbenzoic acid 
• 2231-57-4 Thiocarbohydrazide 
• 3724-10-5 2-(methylthio)benzoic acid 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 87-24-1 ethyl 2-methylbenzoate 
• 2503-66-4 5-(2-methylphenyl)-1,3,4-oxadiazole-2-thiol 

Downstream Products

• 87239-97-2 3-(2-Tolyl)-s-triazolo<3,4-b><1,3,4>thiadiazol-6(5H)-thione 
• 922611-29-8 C₁₈H₁₆N₄OS 
• 922580-31-2 C₁₈H₁₆N₄OS 
• 117376-41-7 6,7-Diphenyl-3-o-tolyl-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 117376-38-2 6-Biphenyl-4-yl-3-o-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 221009-63-8 5-(2-tolyl)-3-mercapto-4-<1'H-2'(3'H)-oxoindol-3'-ylimino>-1,2,4-triazole 
• 1227681-99-3 C₃₀H₂₀N₈S₂ 
• 1251005-85-2 6-(1-adamantyl)-3-(2-methylphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 

Relevant academic research and scientific papers

5-substituent-1, 2, 4-triazole-thioketone Schiff base compound as well as preparation method and application thereof

The invention belongs to the technical field of chemical medicines, and relates to a 5-substituent 1, 2, 4-triazole thioketone Schiff base compound as well as a preparation method and application thereof. An intermediate (I) or an intermediate (II) is subjected to reflux reaction with 3, 5-dimethyl 4-hydroxy benzaldehyde in glacial acetic acid respectively, filtering and drying are performed to obtain the 5-substituent -1, 2, 4-triazole thioketone Schiff base compound. According to the 5-substituent-1, 2, 4-triazole-thioketone Schiff base compound as well as the preparation method and application thereof of the invention, an active group-- imino is introduced into a triazole ring matrix to prepare and synthesize a series of triazole Schiff base compounds with multiple active sites, and thetriazole Schiff base compounds have the advantages of good activity, small dosage, small toxic and side effects, safety and environmental protection; meanwhile, the compounds can be used as crop antifungal agents and can influence the synthesis of fungal cell walls, so that the growth and proliferation of fungi are inhibited, and finally, an antibacterial or bactericidal effect is achieved.

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.

Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles Against MDR Strain of Mycobacterium tuberculosis

Emergence of various forms of resistant strains of Mycobacterium tuberculosis led to the exploration of drugs with novel mechanism of action. Recently econazole, an azole based antitubercular agent, attracted major attention for targeting mycobacterial cytochrome P450. In the present study, we designed novel 1,2,4-triazole derivatives based on econazole moiety and evaluated them for in vitro antitubercular activity against M. tuberculosis H37Rv and multi-drug resistant (MDR) strains of Mycobacterium.

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.

Synthesis, structural characterization and biological studies of neodymium(III) and samarium(III) complexes with mercaptotriazole Schiff bases

A series of neodymium(III) and samarium(III) complexes of type [Ln(L)Cl(H2O)3] have been synthesized with Schiff bases (LH2) derived from 3-(phenyl/substituted phenyl)-4-amino-5-mercapto-1,2,4-triazoles and isatin. The str

Synthesis, anti-HIV activity and Molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole derivatives

A series of novel 3-aryl-6-adamantylmethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 6a-l were synthesized by a simple method with the aim of developing novel HIV non-nucleoside reverse transcriptase inhibitors. All the synthesized compounds were structurally confirmed by spectral analyses. The structure of 6a was unambiguously verified by X-ray structure determination. The synthesized compounds were evaluated for their anti-HIV activity and four analogs displayed moderate inhibitory activity with EC50 values ranging from 10.10 to 12.40 μg mL-1. Molecular docking of 6g with HIV-1 reverse transcriptase was studied to rationalize some structureactivity relationships (SARs).

Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors

A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole,

Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety

Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 μg/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 μg/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 μg/ml. All of the compounds synthesized in the current Letter were characterized by 1H NMR, 13C NMR, infrared and mass spectroscopy.

Synthesis and evaluation of antioxidant properties of novel 1,2,4-triazole-based schiff base heterocycles

A series of 1,2,4-triazole-based Schiff base heterocyclic compounds (5a-f and 8a-i) and phenethylamines (7a-h) were synthesized and evaluated for antioxidant properties by free-radical scavenging, anti-hemolytic activity, lipid peroxidation, and their protective effects against DNA oxidative damage. Compounds 7c, 7d, 7h, 8b, and 8i showed promising DPPH? radical scavenging activity with the level of inhibition between 86.8% and 94%. Compounds 8a, 8b, 8d, 8g, and 8i were effective against the oxidative hemolysis of human erythrocytes and lipid peroxidation, in a dose-dependent manner, with IC50 values in the range of 55.7-80.7 and 53.2-81.2 μg/mL, respectively. Compounds 8a and 8b were effective against oxidative damage on erythrocyte ghost membrane proteins, and 8g and 8i were able to protect against DNA oxidative damage. 1,2,4-Triazole based Schiff base heterocycles (5a-f, 8a-i) and phenethylamines (7a-h) were synthesized and evaluated for their antioxidant properties by free-radical scavenging, anti-hemolytic activity, lipid peroxidation, and their protective effects against DNA oxidative damage.

Synthesis, antiviral, and antimicrobial activity of 1,2,4-triazole thioglycoside derivatives

The reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with glucosyl, galactosyl, lactosyl bromide, and peracetylated ribose under the conventional and microwave irradiation methods afforded the corresponding S-glycosides. Deacetylation of S-glycos