93300-54-0

Usage

Uses

Used in Medicinal Chemistry:
5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazole-3-thiol is used as a pharmaceutical intermediate for the development of drugs targeting various biological pathways. Its unique structure and reactivity make it a promising candidate for the creation of new therapeutic agents.
Used in Chemical Research and Synthesis:
In the field of chemical research and synthesis, 5-(4-chloro-phenyl)-4-phenyl-4H-[1,2,4]triazole-3-thiol is used as a building block for the synthesis of more complex molecules. Its distinctive properties allow for the exploration of new chemical reactions and the creation of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazole-3-thiol is utilized as a key component in the formulation of new drugs within the pharmaceutical industry. Its potential to target specific biological pathways makes it a valuable asset in the development of innovative therapeutics.
Used in Chemical Synthesis Industry:
In the chemical synthesis industry, 5-(4-chloro-phenyl)-4-phenyl-4H-[1,2,4]triazole-3-thiol is employed as a versatile building block for the creation of a wide range of complex molecules. Its unique structure and reactivity contribute to the advancement of chemical synthesis techniques and the development of new compounds with diverse applications.

InChI:InChI=1/C14H10ClN3S/c15-11-8-6-10(7-9-11)13-16-17-14(19)18(13)12-4-2-1-3-5-12/h1-9H,(H,17,19)

Upstream product

• 96134-02-0 C₁₀H₁₂ClN₃OS 
• 62-53-3 aniline 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 74-11-3 para-chlorobenzoic acid 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 103-72-0 phenyl isothiocyanate 
• 93034-60-7 1-[(4′-chlorophenyl)carbonyl-4-phenyl]thiosemicarbazide 
• 104-88-1 4-chlorobenzaldehyde 
• 40546-41-6 ethyl-4-chlorobenzimidate hydrochloride 

Downstream Products

• 150535-87-8 [5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid methyl ester 
• 93300-30-2 2-[5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-N-methyl-acetamide 
• 93300-22-2 [5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid hydrazide 
• 93300-31-3 2-[5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-N-ethyl-acetamide 
• 93300-33-5 2-[5-(4-Chloro-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-N-propyl-acetamide 

Relevant academic research and scientific papers

Synthesis, molecular docking and evaluation of library of 3-mercapto-1,2,4-triazole derivatives as antimicrobial agents

Due to the increasing microbial resistance to antibacterial and antifungal drugs, the development of new antimicrobial agents is an urgent priority. In search of newer antimicrobial agents, a series of 4,5-disubstituted-3-mercapto-1,2,4-triazole derivatives were synthesized from aromatic acids and substituted isothiocyanates. The in silico study was performed to study the binding interactions of the synthesized compounds with the active pocket of CYP51. Among the synthesized 3-mercapto-triazole derivatives, compounds 6r, 6s and 6u exhibited promising antimicrobial activity comparable to standard drugs. The results suggested that the structural modification to 3-mercapto-1,2,4-triazole derivatives could lead to promising antimicrobial scaffolds.

Design, synthesis and biological evaluation of novel 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiols as an anticancer agent

Cellular tumor antigen p53 is significant for cancer prevention and its mutation is most documented genomic change in human cancers. Thus, restoration of p53 function by interruption of the p53-MDM2 interaction opens up a prospect for a nongenotoxic anticancer therapeutic strategy. A novel series of molecules comprising 1,2,4-triazole-3-thiol scaffold were successfully discovered by structure-based designing approach. In silico modules predicted that 5-(4-chlorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol derivatives have draggability and ability to mimic critical binding residues of p53. All target compounds were assayed for their in vitro antiproliferative activity against A549, U87 and HL60 cell lines. Twelve out of sixteen compounds exhibited good in vitro inhibitory activity in micromolar range. Especially, compound 6h possessed acute antitumor activity with IC50 values 3.854, 4.151 and 17.522 μM against three tested cell lines. It represents as a promising lead for further optimization and a template for development of novel antitumor agents.

Novel 1,2,4-triazole derivatives: Design, synthesis, anticancer evaluation, molecular docking, and pharmacokinetic profiling studies

Three novel series of 1,2,4-triazole derivatives were designed and synthesized as potential adenosine A2B receptor antagonists. The design of the new compounds depended on a virtual screening of a previously constructed library of compounds targeting the human adenosine A2B protein. Spectroscopic techniques including 1H nuclear magnetic resonance (NMR) and 13C NMR, and infrared and mass spectroscopy were used to confirm the structures of the synthesized compounds. The in vitro cytotoxicity evaluation was carried out against a human breast adenocarcinoma cell line (MDA-MB-231) using the MTT assay, and the obtained results were compared with doxorubicin as a reference anticancer agent. In addition, in silico studies to propose how the two most active compounds interact with the adenosine A2B receptor as a potential target were performed. Furthermore, a structure–activity relationship analysis was performed, and the pharmacokinetic profile to predict the oral bioavailability and other pharmacokinetic properties was also explained. Four of our designed derivatives showed promising cytotoxic effects against the selected cancer cell line. Compound 15 showed the highest activity with an IC50 value of 3.48 μM. Also, compound 20 revealed an equipotent activity with the reference cytotoxic drug, with an IC50 value of 5.95 μM. The observed IC50 values were consistent with the obtained in silico docking scores. The newly designed compounds revealed promising pharmacokinetic profiles as compared with the reference marketed drug.

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs

Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.

Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity

New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).

New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells

A series of novel 1, 2, 4-triazole/chalcone hybrids was prepared and identified with different spectroscopic techniques. The prepared compounds showed remarkable cytotoxic activity against different cancer cell lines. Compounds 24, 25, 27, 41 and 47 had shown the highest cytotoxicity among the tested compounds against human lung adenocarcinoma A549 cells with IC50 ranging from 4.4 to 16.04 μM compared to cisplatin with IC50 of 15.3 μM. Flow cytometric analysis of the tested compounds showed an increase in the number of apoptotic cells in a dose-dependent manner. The further mechanistic study demonstrated that 1, 2, 4-triazole-chalcone hybrids induced apoptosis via increased level of proapoptotic protein Bax, release of cytochrome c from mitochondria and activation of caspase-3/8/9 proteins. However, general caspase inhibition by the pan-caspase inhibitor, z-VAD-fmk, significantly decreased the apoptosis induced by the tested hybrids, suggesting dependency of apoptosis on activation of the caspase-3 pathway.

Synthesis of 1,2,4-Triazoles via Oxidative Heterocyclization: Selective C-N Bond over C-S Bond Formation

The higher propensity of C-N over C-S bond forming ability was demonstrated, through formal C-H functionalization during the construction of 4,5-disubstituted 1,2,4-triazole-3-thiones from arylidenearylthiosemicarbazides catalyzed by Cu(II). However, ster

A one-pot synthesis of 4,5-disubstituted-1,2,4-triazole-3-thiones on solid support under microwave irradiation

4,5-Di-substituted-1,2,4-triazole-3-thiones (4a-f) have been prepared in one stage from the reaction of acid hydrazide 1 with alkyl or aryl isothiocyanate 2 in the presence of a KOH (10%) solution on the surface of silica gel as well as on the surface of montmorillonite K10 under microwave irradiation. These triazoles have also been prepared from the reaction of 4-substituted-1-aroyl thiosemicarbazides 3a-e, with a KOH (10%) solution on the surface of silica gel under microwave irradiation. Copyright Taylor & Francis Group, LLC.

Syntheses of Substituted 3-Mercapto-1,2,4-triazoles as Potential Antimicrobial Agents

Some hydrazides (3-5) and amides (6-17) have been prepared by reacting 3,4-disubstituted ethyl 1,2,4-triazole-5-mercaptoacetates (1,2) with hydrazines and alkylamines respectively.Treatment of the hydrazides (3,4) with alkyl or aryl isothiocyanates afford