32362-88-2

Usage

Uses

Used in Pharmaceutical Development:
1,2-Dihydro-5-(3-pyridinyl)-3H-1,2,4-triazole-3-thione is used as a chemical intermediate for the development of new medications. Its unique molecular structure makes it a valuable component in the creation of pharmaceuticals targeting various health conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1,2-Dihydro-5-(3-pyridinyl)-3H-1,2,4-triazole-3-thione serves as a key compound for research into the discovery and design of novel therapeutic agents. Its properties are being studied to understand its interaction with biological targets and its potential efficacy in treating specific diseases.

InChI:InChI=1/C7H6N4S/c12-7-9-6(10-11-7)5-2-1-3-8-4-5/h1-4H,(H2,9,10,11,12)

Upstream product

• 88317-41-3 potassium N-(pyridine-4-carbonyl)-hydrazine carbodithiolate 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 
• 79-19-6 thiosemicarbazide 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 553-53-7 Nicotinic acid hydrazide 
• 1452-63-7 picolinic acid hydrazide 
• 75-15-0 carbon disulfide 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 14397-23-0 nicotinoyl thiosemicarbazide 
• 59-67-6 nicotinic acid 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 440638-11-9 3-[4-benzyl-5-(phenylsulfanyl)-4H-1,2,4-triazol-3-yl]pyridine 

Downstream Products

• 134744-88-0 1-Cyclohexylamino-3-(5-pyridin-3-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol 
• 134744-96-0 1-(4-Phenyl-piperazin-1-yl)-3-(5-pyridin-3-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol 

Relevant academic research and scientific papers

Analgesic and Anti-inflammatory Potential of Merged Pharmacophore Containing 1,2,4-triazoles and Substituted Benzyl Groups via Thio Linkage

A plethora of non-steroidal anti-inflammatory drugs are available in the market with adverse side effects like gastrointestinal irritation, bleeding, and ulceration. Currently, the focus of researcher on the development of better, synergistic molecules by the hybridization of two or more active biomolecule or ligands to develop newer derivative possessing good anti-inflammatory activity with minimum side effects. In line with this, the present study was designed to synthesize a series of merged pharmacophore contaning1,2,4-triazoles and substituted benzyl groups via thio linkage. Purity of the derivatives was confirmed by thin-layer chromatography, combustion analysis, and melting point. Structure of these derivatives was set up by determining infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti-inflammatory activities in mice and rats, respectively. In animal studies, the derivative 3-(5-(4-nitrobenzylthio)-4H-1,2,4-triazol-3-yl) pyridine showed more potent analgesic activity, and the derivative 3-(5-(2,4-dimethylbenzylthio)-4H-1,2,4-triazol-3-yl) pyridine showed more potent anti-inflammatory activity as compared with other derivatives. The results of the present study indicate that reaction of pyridine linked 1,2,4-triazole-3-thiol with different substituted benzyl halides to produce merged pharmacophore contaning1,2,4-triazoles and substituted benzyl groups with potent analgesic and anti-inflammatory activities. Docking studies were performed by using Argus lab, and all the derivatives exhibited good docking scores between ?10 and ?12?kcal/mol and were better as compared with standard drugs aspirin and indomethacin against cyclooxygenase-2. Among all compounds, 3j has shown the maximum docking score and found in agreement to in pharmacological activities.

Synthesis, Characterization, Molecular Modeling, and Biological Evaluation of 1,2,4-Triazole-pyridine Hybrids as Potential Antimicrobial Agents

A novel 1,2,4-triazole-pyridine hybrid derivatives were synthesized by the reaction of nicotinohydrazide with carbon disulfide to yield potassium-3-pyridyl-dithiocarbazate (I). This was further cyclized with ammonia solution to yield 5-mercapto-substituted 1,2,4-triazole-pyridine hybrid (II). This was finally reacted with different substituted benzyl derivatives to produce 1,2,4-triazole-pyridine hybrid derivatives (III). The purity of the derivatives was confirmed by thin-layer chromatography and melting point. Structure of these derivatives was set up by determining its infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectroscopy. Further, the synthesized derivatives were evaluated for their in vitro antimicrobial activity against the three Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Acinetbacter baumannii), three Gram-positive bacteria (Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis), and two fungus (Aspergillus clavatus and Candida albicans). Minimal inhibitory concentration was also determined against same microorganism. Out of all synthesized derivatives, two derivatives, that is, 3-(5-(2-bromobenzylthio)-4H-1,2,4-triazol-3-yl)pyridine and 3-(5-(2,4-dibromobenzylthio)-4H-1,2,4-triazol-3-yl)pyridine showing more potent antibacterial activity. Docking studies were performed by using Argus lab, and all the derivatives exhibited good docking scores between ?10.5369 and ?11.8477?kcal/mol and were better as compared with standard drug methotrexate against a dihydrofolate reductase protein fragment from E.?coli and Lactobacillus (4DFR). Among all compounds, 4h has shown the maximum docking score and found in agreement to in vitro antimicrobial studies.

Novel synthesis of condensed heterocyclic systems containing 1,2,4-triazole ring

3-Aryl-6,7-dihydro-s-triazolo[3,4-b][1,3]thiazines and 3-aryl-5,6-dihydro-thiazolo[2,3-c]-s-triazoles were synthesized by nucleophilic substitution of 3-aryl-5-mercapto-1,2,4-triazoles with 1,3-dibromopropane and 1,2-dichloroethane. And the bis-Mannich re

Synthesis, characterization of 1,2,4-triazole Schiff base derived 3d-metal complexes: Induces cytotoxicity in HepG2, MCF-7 cell line, BSA binding fluorescence and DFT study

Two novel Schiff base ligands H2L1 and H2L2 have been synthesized by condensation reaction of amine derivative of 1,2,4-triazole moiety with 2-hydroxy-4-methoxybenzaldehyde. Co(II), Ni(II), Cu(II) and Zn(II) of the synthesized Schiff bases were prepared by using a molar ratio of ligand:metal as 1:1. The structure of the Schiff bases and synthesized metal complexes were established by 1H NMR, UV–Vis, IR, Mass spectrometry and molar conductivity. The thermal stability of the complexes was study by TGA. Fluorescence quenching mechanism of metal complexes 1–4 show that Zn(II) and Cu(II) complex binds more strongly to BSA. In DFT studies the geometries of Schiff bases and metal complexes were fully optimized with respect to the energy using the 6-31?+?g(d,p) basis set. The spectral data shows that the ligands behaves as binegative tridentate. On the basis of the spectral studies, TGA and DFT data an octahedral geometry has been assigned for Co(II), Ni(II), square planar for Cu(II) and tetrahedral for Zn(II) complexes. The anticancer activity were screened against human breast cancer cell line (MCF-7) and human hepatocellular liver carcinoma cell line (Hep-G2). Result indicates that metal complexes shows increase cytotoxicity in proliferation to cell lines as compared to free ligand.

MULTISUBSTITUTED AROMATIC COMPOUNDS AS INHIBITORS OF THROMBIN

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of thrombin, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing a disease or disorder, which disease or disorder is amenable to treatment or prevention by the inhibition of thrombin.

Heterocycles 39. Synthesis, characterization and evaluation of the anti-inflammatory activity of thiazolo[3,2-b][1,2,4]triazole derivatives bearing pyridin-3/4-yl moiety

Abstract: A series of pyridin-3/4-yl-thiazolo[3,2-b][1,2,4]triazole derivatives (5a–g, 6a–g) were synthesised by Hantzsch condensation of 5-pyridin-3/4-yl-1,2,4-triazole-3-thiol and diverse α-halocarbonyl compounds. Different reaction conditions (pH, temperature, solvent) were investigated for the efficient obtention of the target compounds. Under reflux and acidic conditions, the Hantzsch condensation was a one-step reaction. At room temperature and under basic conditions, it was possible to isolate the iminothioether intermediates 3/4a–g. These intermediates were cyclized in a subsequent step by treatment with concentrated sulphuric acid. The obtained compounds were evaluated for their anti-inflammatory activity. Three synthesised pyridyl-thiazolo[3,2-b][1,2,4]triazole derivatives (6c, 6d, 6f) were found to be good anti-inflammatory agents. Graphical Abstract: [InlineMediaObject not available: see fulltext.].

Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents

Resistance among dormant mycobacteria leading to multidrug-resistant and extremely drug-resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram-negative and Gram-positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100?μg/ml against THP-1, A549, and PANC-1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.

1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY

Disclosed herein are novel five membered heterocyclic compounds of Formula (I) wherein, X is S or SO2; n is 0, 1; m is1 or 2; Y is N, O or S; R2 independently represents H or alkyl or halo selected from -CI, -F; or -CF3, or -OH or-NH2 or - NO2; and R1 independently represents H or C1 to C5 straight or branched chain alkyl, alkenyl, alkynyl or a group -(CH2)5Br or pyrrolidine or - NHR' wherein R' is H or isopropyl or (II) or (III) which selectively act against dormant pathogenic tuberculi bacilli and exhibit antiproliferative activities and for treatment of a disease or disorder associated with GroEL1/GroEL2 activity. The invention relates to a process for preparation of novel five membered heterocyclic compounds of Formula I and to pharmaceutical compositions thereof.

Diaryl-Substituted Azolylthioacetamides: Inhibitor Discovery of New Delhi Metallo-β-Lactamase-1 (NDM-1)

The emergence and spread of antibiotic-resistant pathogens is a global public health problem. Metallo-β-lactamases (MβLs) such as New Delhi MβL-1 (NDM-1) are principle contributors to the emergence of resistance because of their ability to hydrolyze almost all known β-lactam antibiotics including penicillins, cephalosporins, and carbapenems. A clinical inhibitor of MBLs has not yet been found. In this study we developed eighteen new diaryl-substituted azolylthioacetamides and found all of them to be inhibitors of the MβL L1 from Stenotrophomonas maltophilia (KiiiII ion(s) preferentially via the triazole moiety, while other moieties interact mostly with the conserved active site residues Lys224 (CcrA, NDM-1, and ImiS) or Ser221 (L1).

MULTISUBSTITUTED AROMATIC COMPOUNDS AS SERINE PROTEASE INHIBITORS

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of kallikrein, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing certain diseases or disorders, which disease or disorder is amenable to treatment or prevention by the inhibition of kallikrein.