40207-01-0

Usage

Uses

Used in Chemical Research and Organic Synthesis:
3-Methylphenylthiosemicarbazide is used as a key intermediate in the synthesis of various chemical compounds and derivatives. Its unique structure allows for the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
3-Methylphenylthiosemicarbazide is used as a precursor in the development of pharmaceutical compounds. Its potential biological activities, such as antiviral and antimicrobial properties, make it a promising candidate for the creation of new drugs to combat various diseases.
Used in Biocidal Applications:
3-Methylphenylthiosemicarbazide is used as an active ingredient in biocidal products. Its antimicrobial properties can be harnessed to create solutions that effectively control the growth of harmful microorganisms, contributing to improved hygiene and sanitation in various settings.
Used in Agricultural Applications:
3-Methylphenylthiosemicarbazide is used in the development of agricultural chemicals, such as pesticides and fungicides. Its potential to combat harmful organisms can help protect crops and enhance agricultural productivity.

InChI:InChI=1/C8H11N3S/c1-6-3-2-4-7(5-6)10-8(12)11-9/h2-5H,9H2,1H3,(H2,10,11,12)

Upstream product

• 621-30-7 3-methylphenyl isothiocyanate 
• 53278-57-2 m-Toluidino-dithiocarbamyl-essigsaeure 
• 108-44-1 1-amino-3-methylbenzene 
• 53662-45-6 N-(m-tolyl)-dithiocarbamic acid 

Downstream Products

• 103989-87-3 3-m-tolylthiocarbamoyl-carbazic acid ethyl ester 
• 133131-83-6 1-(4-bromo-phenylcarbamoyl)-4-m-tolyl thiosemicarbazide 
• 7701-04-4 3-phenyl-propenal 4-m-tolyl-thiosemicarbazone 
• 103753-99-7 [1,3,4]thiadiazol-2-yl-m-tolyl-amine 
• 2209-27-0 hydrazine-N,N'-dicarbothioic acid bis-(3-methyl-anilide) 
• 52494-32-3 5-(m-methylphenylamino)-1,3,4-thiadiazolium-2-thiolate 
• 57165-97-6 3-(4-m-tolyl-thiosemicarbazonomethyl)-rifamycin 
• 41430-88-0 [1,2,3,4]thiatriazol-5-yl-m-tolyl-amine 
• 67420-00-2 N,N'-di-m-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 260244-12-0 6-amino-5-oxo-2-m-tolylimino-[1,3,4]thiadiazinane-6-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones

In this work, novel 5-fluoro-1-methyl/ethyl-1H-indole-2,3-dione 3-[4-(substituted phenyl)-thiosemicarbazones] 6a-n and 7a-n were synthesized. The antiviral effects of the compounds were tested against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV in HEL cell cultures using acyclovir and ganciclovir as standards, and Coxsackie B4 virus in Vero cell cultures using ribavirin and mycophenolic acid as standards. R2 ethyl substituted 7 derivatives were found effective against viruses tested. R1 4-CF3 substituted 7d, R1 4-OCH3 substituted 7 g and R1 3-Cl substituted 7 l showed activity against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV. Whereas only R1 4-Br substituted 7n has selective activity against coxsackie B4 virus. Molecular modeling studies of 7d and 7l were performed to determine binding side on HSV-1 glycoprotein B and D, HSV-2 glycoprotein B structures.

Microwave-assisted synthesis and antibacterial activity of novel chenodeoxycholic acid thiosemicarbazone derivatives

A rapid and efficient method for the synthesis of novel chenodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave irradiation is reported. Ten novel compounds have been synthesised in good yields. Their structures were elucidated by 1H NMR, IR, ESI-MS spectra and elemental analysis. Preliminary results showed that some of these compounds possess inhibitory effects against S. typhimurium and E. coli.

SAR studies of 4-pyridyl heterocyclic anilines that selectively induce autophagic cell death in von Hippel-Lindau-deficient renal cell carcinoma cells

We recently identified a class of pyridyl aniline thiazoles (PAT) that displayed selective cytotoxicity for von Hippel-Lindau (VHL) deficient renal cell carcinoma (RCC) cells in vitro and in vivo. Structure-activity relationship (SAR) studies were used to develop a comparative molecular field analysis (CoMFA) model that related VHL-selective potency to the three-dimensional arrangement of chemical features of the chemotype. We now report the further molecular alignment-guided exploration of the chemotype to discover potent and selective PAT analogues. The contribution of the central thiazole ring was explored using a series of five- and six-membered ring heterocyclic replacements to vary the electronic and steric interactions in the central unit. We also explored a positive steric CoMFA contour adjacent to the pyridyl ring using Pd-catalysed cross-coupling Suzuki-Miyaura, Sonogashira and nucleophilic displacement reactions to prepare of a series of aryl-, alkynyl-, alkoxy- and alkylamino-substituted pyridines, respectively. In vitro potency and selectivity were determined using paired RCC cell lines: the VHL-null cell line RCC4 and the VHL-positive cell line RCC4-VHL. Active analogues selectively induced autophagy in RCC4 cells. We have used the new SAR data to further develop the CoMFA model, and compared this to a 2D-QSAR method. Our progress towards realising the therapeutic potential of this chemotype as a targeted cytotoxic therapy for the treatment of RCC by exploiting the absence of the VHL tumour suppressor gene is reported.

Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors

A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.

Novel bis(thiosemicarbazones) of the 3,5-diacetyl-1,2,4-triazol series and their platinum(ii) complexes: chemistry, antiproliferative activity and preliminary nephrotoxicity studies

The preparation and characterization of three novel 4N- monosubstituted bis(thiosemicarbazone) ligands of 3,5-diacetyl-1,2,4-triazol series and their dinuclear platinum complexes are described. The crystal and molecular structure of the [Pt(μ-H

A series of α-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIα catalytic activity

A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase IIα catalytic inhibitor. Its inhibition on topoisomerase IIα was due to direct interaction with the ATPase domain of topoisomerase IIα which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase IIα.

Efficient synthesis of 1,3,4-thiadiazoles using hydrogen bond donor (thio)urea derivatives as organocatalysts

(Chemical Equation Presented) A simple and efficient procedure for the synthesis of 1,3,4-thiadiazoles has been achieved using thiourea as organocatalyst. In this study, the steric and electronic effects using structurally different derivatives of urea and thiourea in different solvents were evaluated. The best yields and the rate of the reactions were obtained using 30 mol % of thiourea as catalyst in acetonitrile at room temperature. The molecular structures of the products were established by 1H and 13C NMR spectral data.

Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines

Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, 1H and 13C NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis.

Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica

The cyclization of chalcone with N-4 substituted thiosemicarbazides under basic condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. Structure-activity relationship shows that the compound with aromatic substituents at the thiocarbamoyl group was more active than those with the cyclic groups. However, it was clear from the IC50 values that the compounds 15 and 20 are more active and both showed a structural resemblance having an electron withdrawing groups attached to the phenyl ring. MTT assay showed that all the compounds are non-toxic to human kidney epithelial cell line.

Synthesis, spectral studies and in vitro antibacterial activity of steroidal thiosemicarbazone and their palladium (Pd (II)) complexes

We investigated the antibacterial activity of some new steroidal thiosemicarbazone and their Pd(II) metal complexes. Metal complexes were prepared from the reaction of steroidal thiosemicarbazone with [Pd(DMSO)2Cl2]. Coordination via