81518-26-5

Basic information

• Product Name: (6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one
• CAS NO: 81518-26-5
• Molecular Formula: C₁₄H₁₁N₃OS
• Molecular Weight: 269.3216
• Mol File: 81518-26-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 407.7°C at 760 mmHg
• Flash Point: 200.3°C
• Density: 1.43g/cm³
• Vapor Pressure: 7.42E-07mmHg at 25°C
• Refractive Index: 1.762
• CAS DataBase Reference: (6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one(81518-26-5)
• EPA Substance Registry System: (6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one(81518-26-5)

Safety Data

• Hazardous Substances Data: 81518-26-5(Hazardous Substances Data)

Usage

Description

(6Z)-6-(4-phenyl-5-thioxo-1,2,4-triazolidin-3-ylidene)cyclohexa-2,4-dien-1-one is a complex organic compound characterized by a cyclohexa-2,4-dien-1-one ring system with a 1,2,4-triazolidine-3-thione moiety and a phenyl group attached. This chemical structure suggests potential biological activities due to the presence of the triazolidine ring, which is known for its diverse pharmacological properties. However, further research and investigation are required to fully understand the compound's properties and potential applications.

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 
• 119-36-8 methyl salicylate 
• 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 

Downstream Products

• 122448-07-1 bis-[5-(2-hydroxy-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-yl]-disulfide 
• 81518-33-4 2-(5-Methylsulfanyl-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 
• 81518-34-5 2-(5-Ethylsulfanyl-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 
• 81518-37-8 2-(5-Butylsulfanyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-phenol 
• 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 
• 18199-85-4 2-[5-(2-hydroxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thioacetic acid 

Relevant articles and documents

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.

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.

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 (