70452-38-9

Basic information

• Product Name: 4-PHENYL-1-(3,4,5-TRIMETHOXYBENZOYL)THIOSEMICARBAZIDE
• Synonyms: 4-PHENYL-1-(3,4,5-TRIMETHOXYBENZOYL)THIOSEMICARBAZIDE;3,4,5-trimethoxy-N-[(phenylcarbamothioyl)amino]benzamide
• CAS NO: 70452-38-9
• Molecular Formula: C₁₇H₁₉N₃O₄S
• Molecular Weight: 361.42
• Mol File: 70452-38-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-PHENYL-1-(3,4,5-TRIMETHOXYBENZOYL)THIOSEMICARBAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYL-1-(3,4,5-TRIMETHOXYBENZOYL)THIOSEMICARBAZIDE(70452-38-9)
• EPA Substance Registry System: 4-PHENYL-1-(3,4,5-TRIMETHOXYBENZOYL)THIOSEMICARBAZIDE(70452-38-9)

Safety Data

• Hazardous Substances Data: 70452-38-9(Hazardous Substances Data)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 3291-03-0 3,4,5-trimethoxybenzohydrazide 
• 118-41-2 Eudesmic acid 
• 6178-44-5 ethyl 3,4,5-trimethoxybenzoate 

Downstream Products

• 35314-01-3 2-(3,4,5-trimethoxyphenyl)-5-(phenylamino)-1,3,4-thiadiazole 
• 80987-70-8 Phenyl-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-amine 
• 70452-47-0 4-phenyl-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol 
• 327094-29-1 2-[5-(3,4,5-trimethoxyphenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-1-phenylethanone 
• 150535-94-7 methyl 2-<<4-phenyl-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-yl>thio>propionate 
• 70452-56-1 [4-phenyl-5-(3,4,5-trimethoxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid ethyl ester 
• 91759-76-1 [4-Phenyl-5-(3,4,5-trihydroxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetic acid 
• 18204-69-8 5-(3,4,5-trimetossifenil)-4-fenil-3-carbossimetiltio-4H-1,2,4-triazolo 

Relevant articles and documents

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.

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.

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

1,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors: Synthesis, anti-inflammatory, ulceroginicity and antiproliferative activities

A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity and antiproliferative activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their ketone intermediates and indomethacin. The NO-donating oximes 7i and 7k achieved remarkable cell growth inhibition activity against most of the tested cell lines. Compound 7k was found to be with high selectivity against CNS subpanel with selectivity ratio of 11.99 at GI 50 level.

New nitric oxide donating 1,2,4-triazole/oxime hybrids: Synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities

A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their intermediate ketones and indomethacin. The NO-donating oxime 6i revealed significant activity against renal cancer A498 cell lines with 50.52 cell growth inhibition.

Synthesis and crystal structure of novel sulfone derivatives containing 1,2,4-triazole moieties

Some 3-(Substituted methylthio)-4-phenyl-5-(3,4,5-trimethoxyphenyl)-4H-1,2, 4-triazole derivatives were synthesized in six steps starting from easily accessible gallic acid. The resulting sulfides were then catalytically oxidized to the title sulfones with H2O2. The products were obtained in high yield under mild conditions and practically devoid of any by-products. The structures were confirmed by elemental analysis, IR, 1H- and 13C-NMR spectral data. Furthermore, a detailed X-ray crystallography structural analysis of model triazole 7g was carried out.

1,3,4-Thiadiazoles. Regioselective O-demethylation on dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides with sulphuric acid

Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-substituted amino-1,3,4-thiadiazoles 4a-g. Meanw

Synthesis and biological testing of certain 1,3,4-oxadiazole and 1,2,4-triazole derivatives as potential antimicrobial agents

A series of hydrazones, thiosemicarbazides and 2,5-disubstituted-1,3,4-oxadiazoles bearing 3,4,5-trimethoxyphenyl moiety was synthesized. Furthermore, the reaction of the prepared 1-(3,4,5-trimethoxybenzoyl)thiosemicarbazide and 3-(3,4,5-trimethoxy-phenyl