81518-26-5

Usage

Uses

Used in Pharmaceutical Industry:
(6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one is used as a potential pharmaceutical compound for [application reason] due to its triazolidine ring, which is known for its diverse pharmacological properties.
Used in Chemical Research:
In the field of chemical research, (6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one serves as a subject for further investigation to explore its chemical properties, reactivity, and potential applications in various chemical processes.

Upstream product

• 37536-32-6 2-(2-hydroxybenzoyl)-N-phenylhydrazincarbothioamide 
• 936-02-7 2-Hydroxybenzoylhydrazine 
• 103-72-0 phenyl isothiocyanate 
• 1044147-91-2 3-[(2,3-dihydroxyprop-1-yl)thio]-5-(o-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazole 
• 75-15-0 carbon disulfide 
• 62-53-3 aniline 
• 119-36-8 methyl salicylate 

Downstream Products

• 122448-07-1 bis-[5-(2-hydroxy-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-yl]-disulfide 
• 18199-85-4 2-[5-(2-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thioacetic acid 
• 1044147-91-2 3-[(2,3-dihydroxyprop-1-yl)thio]-5-(o-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazole 
• 1044147-89-8 3-[(3-hydroxyprop-1-yl)thio]-5-(o-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazole 
• 831214-77-8 3-[(2-hydroxyethyl)thio]-5-(o-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazole 
• 1044147-86-5 5-(2-hydroxyphenyl)-4-phenyl-3-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosylthio)-4H-1,2,4-triazole 
• 1044147-85-4 5-(o-hydroxyphenyl)-4-phenyl-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)-4H-1,2,4-triazole 
• 1044147-87-6 5-(o-hydroxyphenyl)-4-phenyl-3-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosylthio)-4H-1,2,4-triazole 
• 1375488-86-0 1,3-bis[4-phenyl-5(2'-hydroxyphenyl)-1,2,4-triazol-3-yl]mercaptopropane 
• 81518-37-8 2-(5-Butylsulfanyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol 
• 81518-36-7 2-(4-Phenyl-5-propylsulfanyl-4H-[1,2,4]triazol-3-yl)-phenol 
• 81518-33-4 2-(5-Methylsulfanyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol 
• 81518-34-5 2-(5-Ethylsulfanyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol 
• 81518-35-6 2-(5-Allylsulfanyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol 

Relevant academic research and scientific papers

Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting D-alanyl-D-alanine ligase in bacterio

D-Alanyl-D-alanine ligase (Ddl) is a validated and attractive target among the bacterial enzymes involved in peptidoglycan biosynthesis. In the present work, we investigated the pharmacomodulations of the benzoylthiosemicarbazide scaffold to identify new Ddl inhibitors with antibacterial potency. Five novel series of thiosemicarbazide analogues, 1,2,4-thiotriazole-3-thiones, 1,3,4-thiadiazoles, phenylthiosemicarbazones, diacylthiosemicarbazides and thioureas were synthesized via straightforward procedures, then tested against Ddl and on susceptible or resistant bacterial strains. Among these, the thiosemicarbazone and thiotriazole were identified as the most promising scaffolds with Ddl inhibition potency in the micromolar range. Antimicrobial evaluation of salicylaldehyde-4(N)-(3,4-dichlorophenyl) thiosemicarbazone 33, one of the best compounds in our study, revealed interesting antimicrobial activities with values of 3.12–6.25 μM (1.06–2.12 μg/mL) against VRE strains and 12.5–25.0 μM (4.25–8.50 μg/mL) towards MRSA and VRSA strains. A detailed mechanistic study was conducted on the Ddl inhibitors 4-(3,4-dichlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 20 and compound 33, and revealed a bactericidal effect at 5 × MIC concentration after 7 h and 24 h, respectively, and a bacteriostatic effect at 1 × MIC or 2 × MIC without any sign of bacterial membrane disruption at these lower concentrations. Finally, 20 and 33 were proved to target Ddl in bacterio via intracellular LC-MS dosage of D-Ala, L-Ala and D-Ala-D-Ala. Although, at this stage, our results indicate that other mechanisms might be involved to explain the antimicrobial potency of our compounds, their ability to inhibit the growth of strains resistant to usual antibiotics, as well as strains that express alternative ligases, sets the stage for the development of new antimicrobial agents potentially less sensitive to resistance mechanisms.

Design, Synthesis and Antibacterial Evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione Hybrids

A new class of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin (CPFX)-1,2,4-triazole-5(4H)-thione hybrids 6a?–?6o was designed, synthesized and evaluated for their in?vitro antibacterial activities against a panel of clinically important drug-sensitive and d

Synthesis and biological evaluation of 1, 2, 4-triazoles and 1, 3, 4-oxadiazoles derivatives linked to 1, 4-dihydropyridines scaffold

A series of diethyl-2, 6-dimethyl-4-phenyl-1, 4-dihydropyridine-3, 5-dicarboxylate derivative coupled to 1, 3, 4-oxadiazole-5-thiones and 1, 2, 4-triazole-5-thiones moieties at C2, C6 positions of 1, 4-dihydropyridine ring system was prepared. This linkage was carried out by the reaction of 1, 3, 4-oxadiazole-5-thiones and 1, 2, 4-triazole-5-thiones with 2, 6-dibromomethyl-3, 5-diethoxycarbonyl-4-phenyl-1, 4-dihydropyridine in the presence of potassium carbonate as a weak base and dry acetone as the solvent. The newly synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR spectral data, elemental analysis and FAB-MS. The synthesized compounds were tested for their antimicrobial and antifungal activity against Escherichia coli and Aspergillus fumigatus in vitro in comparison with Enrofloxacin and Amphotericin as the reference drugs which are normally used for treating such infections. The synthetic compounds showed different inhibition zones against tested bacteria and fungi. Compound 8d showed more antagonistic activity against E. coli and A. fumigatus.

Synthesis of a series of novel tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole and 1,3,4-oxadiazole derivatives

A series of tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones derivatives at lower rim were synthesized by the reaction of 1,2,4-triazole-5-thione and 1,3,4-oxadiazole-5-thione with 5,11,17,23-tetra-tert-butyl-25,27-bis(3-bromopropoxy)-26,28-dihydroxycalix[4]arene (2). The synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR spectral data, elemental analysis and ESI-MS.

Search for factors affecting antibacterial activity and toxicity of 1,2,4-triazole-ciprofloxacin hybrids

A series of 1,2,4-triazole-based compounds was designed as potential antibacterial agents using molecular hybridization approach. The target compounds (23-44) were synthesized by Mannich reaction of 1,2,4-triazole-3-thione derivatives with ciprofloxacin (

Novel synthesis of 1,2,4-triazolophanes and 1,3,4-oxadiazolophanes: A dieckmann condensation approach

The Dieckmann condensation has been used for the first time for the syntheses of novel 1,2,4-triazolophanes and 1,3,4-oxadiazolophanes. The bis-1,3,4-oxadiazol-2-thiols 1a and 1b were reacted with ethyl bromoacetate to give the diesters 2a and 2b. Diester

Synthesis of 5-aryl-3-glycosylthio-4-phenyl-4H-1,2,4-triazoles and their acyclic analogs under conventional and microwave conditions

Under microwave irradiation (MWI), 4-phenyl-5-substituted-4H-1,2,4- triazole-3-thiol derivatives 7 and 8 were synthesized in a good yield by intramolecular cyclization of the aroyl phenyl thiosemicarbazides 5 and 6. The respective triazolylglycosides (Str-glycosides) 12-17 were obtained by reaction of triazoles 7 and 8 with glycosyl halides 9-11 in dry acetone in the presence of potassium carbonate as base under both conventional and MWI conditions. Alkylation of 7 and 8 with haloalchols 18-20 in boiling ethanolic solution containing sodium ethoxide as a base gave the corresponding alkylated analogs 21-26. MWI conditions led to higher yield in shorter reaction time than the conventional method. Treatment of 26 with tosyl chloride gave the unexpected product 29 and not 27 or 28. Oxidation of 26 with sodium metaperiodate afforded triazole 8 and not the aldehyde 30. Attempted glycosylation and alkylation of the phenolic OH group in triazole 8 were unsuccessful; this was proved by theoretical calculations using the AM1 semi-empirical method. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.

Synthesis and Antiinflammatory Activity of Some New 3-(o-Substituted phenyl)-4-substituted-phenyl-5-alkyl/alkenyl-mercapto-1H-1,2,4-triazoles

Eighteen 3-(o-substituted phenyl)-4-substituted-phenyl-5-alkyl/alkenyl-mercapto-1H-1,2,4-triazoles (IVa-r) have been synthesized by the reaction of 3-(o-substituted phenyl)-4-substituted-phenyl-5-mercapto-1H-1,2,4-triazoles (IIIa-d) with alkyl/alkenyl hal