36951-41-4

Basic information

• Product Name: 2-(2-(4-methylbenzylidene)hydrazinyl)thiazol-4(5H)-one
• Synonyms: 2-(2-(4-methylbenzylidene)hydrazinyl)thiazol-4(5H)-one
• CAS NO: 36951-41-4
• Molecular Weight: 233.294
• Mol File: 36951-41-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(2-(4-methylbenzylidene)hydrazinyl)thiazol-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-(4-methylbenzylidene)hydrazinyl)thiazol-4(5H)-one(36951-41-4)
• EPA Substance Registry System: 2-(2-(4-methylbenzylidene)hydrazinyl)thiazol-4(5H)-one(36951-41-4)

Safety Data

• Hazardous Substances Data: 36951-41-4(Hazardous Substances Data)

Upstream product

• 125611-77-0 3-{[1-p-Tolyl-meth-(Z)-ylidene]-amino}-2-{[1-p-tolyl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 104-87-0 4-methyl-benzaldehyde 
• 79-19-6 thiosemicarbazide 
• 105-36-2 ethyl bromoacetate 
• 5349-28-0 thiocyanato-acetic acid ethyl ester 
• 4702-76-5 4,4'-dimethylbenzaldazine 
• 6327-31-7 1,5-bis-(4-methyl-benzylidene)-thio carbonohydrazide 
• 125611-79-2 3-{[1-Phenyl-meth-(Z)-ylidene]-amino}-2-{[1-p-tolyl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 125611-82-7 3-Amino-2-{[1-p-tolyl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 5706-83-2 4-methylbenzaldehyde thiosemicarbazone 
• 125611-76-9 C₁₆H₁₆N₄S 
• 51176-64-8 C₉H₁₂N₄S 

Relevant articles and documents

An environmentally benign one pot synthesis of pyrazole substituted-2-hydrazolyl-4-Thiazolidinones

Background: Thiazolidinone and pyrazoles are promising heterocyclic systems enormously contributing to medicinal chemistry and when pyrazole nucleus was incorporated in other biodynamic heterocycles, the resulting molecules have displayed an increased spectrum of biological activities. There are several synthetic routes for the synthesis of thiazolidinone molecules but are having certain lacunas like, need of catalysts and desiccants, higher reaction temperature, longer reaction time, organic solvents and tedious work up procedure. Methods: Here an ultrasound promoted one pot multicomponent protocol is developed for 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-Thiazolidinones (6a-g). Here freshly prepared substrates, 3-(4-substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehydes (5a-g), have been condensed with thiosemicarbazide (2) and ethylbromo acetate (3) in aqueous emulsion of surfactant, CTAB under ultrasonication. Results: In our study the titled compounds 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-thiazolidinones obtained with good to excellent yields using 20 mol% aqueous emulsion of CTAB under ultrasound irradiation at 60°C. Conclusion: First time we have provided an environmentally friendly ultrasound promoted synthetic route to 2-hydrazolyl-4-Thiazolidinones (4a-g) and biologically significant 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-Thiazolidinones (6a-g) using aqueous emulsion of CTAB as reaction medium. The method offered several advantages such as operational simplicity, easy work-up procedure, shorter reaction times and high yields. The protocol is safe, economic and convenient for obtaining library of 2-hydrazolyl/imino-4-Thiazolidinones rapidly.

Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors

Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 μM for EGFR and IC50 = 0.42 μM for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent.

Synthesis and Structure of Some Thiazole Derivatives

The addition of thiosemicarbazones 1 to α-halo acids 2 is shown to give 2-hydrazino-2-thiazolin-4-ones 3 and not 3-substituted 2-imino-3-(methyleneimino)thiazolidin-4-ones 4.The independent synthesis of 2-thiazolin-4-one derivatives 3 is also described.