13153-01-0

Basic information

• Product Name: 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE
• Synonyms: 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE;2-benzoyl-N-phenylhydrazine-1-carbothioamide
• CAS NO: 13153-01-0
• Molecular Formula: C₁₄H₁₃N₃OS
• Molecular Weight: 271.34
• Mol File: 13153-01-0.mol

Chemical Properties

• Appearance: /
• Density: 1.308g/cm³
• Refractive Index: 1.697
• CAS DataBase Reference: 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE(13153-01-0)
• EPA Substance Registry System: 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE(13153-01-0)

Safety Data

• Hazardous Substances Data: 13153-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE is used as a precursor in the development of new drugs and pharmaceuticals for its potential biological activities, including antimicrobial and anticancer properties.
Used in Research as a Chemical Reagent:
In the scientific community, 1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE is utilized as a chemical reagent, facilitating various research processes and experiments that require its unique chemical structure.
Used in Organic Synthesis as a Building Block:
1-BENZOYL-4-PHENYL-3-THIOSEMICARBAZIDE is employed as a building block in the synthesis of other organic compounds, contributing to the creation of novel chemical entities with potential applications in various fields.

InChI:InChI=1/C14H13N3OS/c18-13(11-7-3-1-4-8-11)16-17-14(19)15-12-9-5-2-6-10-12/h1-10H,(H,16,18)(H2,15,17,19)

Upstream product

• 98-88-4 benzoyl chloride 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 64-17-5 ethanol 
• 103-72-0 phenyl isothiocyanate 
• 613-94-5 benzoic acid hydrazide 
• 3004-42-0 5-phenyl-1,3,4-oxadiazole-2(3H)-thione 
• 62-53-3 aniline 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 93-89-0 benzoic acid ethyl ester 
• 93-99-2 benzoic acid phenyl ester 
• 93-58-3 benzoic acid methyl ester 
• 637-51-4 isothiocyanatobenzene 
• 5285-87-0 phenyl thiocyanate 
• 65-85-0 benzoic acid 

Downstream Products

• 1437-57-6 5-Phenyl-2-phenylamino-1,3,4-thiadiazol 
• 6596-82-3 4,5-diphenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 1148-89-6 2-phenylamino-5-phenyl-1,3,4-oxadiazole 
• 14331-27-2 1-acetyl-2-benzoylhydrazine 
• 63586-61-8 N-phenyl-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 15129-16-5 (4,5-diphenyl-4H-[1,2,4]triazol-3-yl)-phenyl-amine 
• 102452-34-6 N-(4-phenyl-2-phenylimino-thiazol-3-yl)-benzamide 
• 33238-09-4 1-benzoyl-S-methyl-4-phenyl-iso thiosemicarbazide 
• 6596-82-3 4,5-diphenyl-4H-1,2,4-triazole-3-thiol 
• 613-94-5 benzoic acid hydrazide 
• 102-08-9 N,N-diphenylthiourea 
• 54559-45-4 [(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetic acid 
• 91759-70-5 ethyl 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate 
• 33199-66-5 3-methylsulfanyl-4,5-diphenyl-4H-[1,2,4]triazole 

Relevant articles and documents

Vibrational and quantum chemical investigation of cyclization of thiosemicarbazide group in 1-benzoyl-4-phenyl-3-thiosemicarbazide

1-Benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) was treated with acid - base in one sequence and base - acid in other sequence, both of which lead to ring formation of thiosemicarbazide group, giving N-phenyl-5-phenyl-1,3, 4-thiadiazol-2-amine (Hppta) in the first case and 4,5-diphenyl-2,4-dihydro-1,2, 4-triazole-3-thione (Hdptt) in the second case. The primary (H3bpt) as well as the resulting compounds (Hppta & Hdptt) has been characterized by elemental analyses, NMR, FTIR and Raman spectroscopic techniques. The quantum chemical calculations of the compounds are performed using DFT/B3LYP/6311G(d,p) method for geometry optimizations and also for prediction of the molecular properties. The cyclization is confirmed by disappearance of many bands belonging to the open chain subgroups of H3bpt such as; NH stretching, NH bending, CN stretching, NH puckering, CO stretching etc. The ring formation of 1-benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) has been further confirmed by the appearance of many bands belonging to the closed ring of thiosemicarbazide in the resulting compounds Hppta and Hdptt.

Efficiency of Some Phenylthiosemicarbazide Derivatives in Retarding the Dissolution of Al in NaOH Solution

Five derivatives of phenylthiosemicarbazide have been prepared and treated as inhibitors for the corrosion of aluminium in 2 M sodium hydroxide.All the five substances afford 98,5 to 75percent protection to aluminium in sodium hydroxide. 1-(Methoxybenzoyl

Synthesis, characterization and antioxidant activities of semicarbazide and thiosemicarbazide derivatives

In this research work Semicarbazide, thiosemicarbazide derivatives 3 to 25 were synthesized by conventional methods with high percentage yield and reaction rate. 1H-NMR and EIMS spectroscopic techniques were used to elucidate the structure of t

A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives

A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room tempera

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 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).

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.

Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β- d -ribofuranose 2′-Oxidase

We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure-activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H37Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 μM, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-β-d-ribofuranose 2′-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.

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.

1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting D-alanine-D-alanine ligase in bacterio

The bacterial cell wall and the enzymes involved in peptidoglycan synthesis are privileged targets for the development of novel antibacterial agents. In this work, a series of 1-(2-hydroxybenzoyl)-thiosemicarbazides inhibitors of D-Ala-D-Ala ligase (Ddl) were designed and synthesized in order to target resistant strains of bacteria. Among these, the 4-(3,4-dichlorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide 29 was identified as a potent Ddl inhibitor with activity in the micromolar range. This compound, possessing strong antimicrobial activity including against multidrug resistant strains, was proven to act through a bactericidal mechanism and demonstrated very low cytotoxicity on THP-1 human monocytic cell line. Inhibition of Ddl activity by 29 was confirmed in bacterio using UPLC-MS/MS by demonstrating an increase in D-Ala intracellular pools accompanied by a commensurate decrease in D-Ala-D-Ala. Further structure-activity relationships (SARs) studies provided evidence that the hydroxyl substituent in the 2-position (R1) of the benzoylthiosemicarbazide scaffold is essential for the enzymatic inhibition. This work thus highlights the 1-(2-hydroxybenzoyl)-thiosemicarbazide motif as a very promising tool for the development of novel antibacterial compounds acting through an interesting mechanism of action and low cytotoxicity.