23969-11-1

Basic information

• Product Name: 2-(2-benzylidenehydrazinyl)-1,3-thiazol-4(5H)-one
• CAS NO: 23969-11-1
• Molecular Formula: C₁₀H₉N₃OS
• Molecular Weight: 219.263
• Mol File: 23969-11-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 366.6°C at 760 mmHg
• Flash Point: 175.5°C
• Density: 1.34g/cm³
• Vapor Pressure: 1.45E-05mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 2-(2-benzylidenehydrazinyl)-1,3-thiazol-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-benzylidenehydrazinyl)-1,3-thiazol-4(5H)-one(23969-11-1)
• EPA Substance Registry System: 2-(2-benzylidenehydrazinyl)-1,3-thiazol-4(5H)-one(23969-11-1)

Safety Data

• Hazardous Substances Data: 23969-11-1(Hazardous Substances Data)

Usage

Chemical structure

2-(2-benzylidenehydrazinyl)-1,3-thiazol-4(5H)-one, containing a thiazole ring with a benzylidenehydrazine group.

Potential biological activities

as an anti-cancer agent and an antibacterial agent.

Promising results

in inhibiting the growth of cancer cells, making it a potential candidate for the development of new anti-cancer drugs.

Antibacterial properties

indicating its potential use in the development of new antibiotics.

Corrosion inhibition

potential as a corrosion inhibitor in metal surfaces.

Versatile compound

with potential applications in various fields, including medicine and material science.

Upstream product

• 1627-73-2 1-benzylidene thiosemicarbazide 
• 587-65-5 N-chloroacetyl-aniline 
• 79-11-8 chloroacetic acid 
• 5349-28-0 thiocyanato-acetic acid ethyl ester 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 100-52-7 benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 32003-36-4 2-hydrazino-1,3-thiazol-4(5H)-one 
• 119023-39-1 3-benzylidenamino-thiazolidine-2,4-dione-2-benzylidenehydrazone 
• 125611-80-5 3-Amino-2-{[1-phenyl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 125611-78-1 2-{[1-Phenyl-meth-(E)-ylidene]-hydrazono}-3-{[1-p-tolyl-meth-(Z)-ylidene]-amino}-thiazolidin-4-one 
• 5351-58-6 benzaldehyde thiocarbohydrazone 
• 6956-33-8 dibenzylidenethiocarbohydrazide 
• 125611-76-9 C₁₆H₁₆N₄S 

Downstream Products

• 1627-70-9 benzaldehyde (5-benzylidene-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 78559-15-6 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-{[1-phenyl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 103726-47-2 2-(4-Oxo-2-phenyl-thiazolidin-3-ylamino)-thiazol-4-one 
• 494582-64-8 1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3,5-diphenyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 494582-74-0 1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3-phenyl-5-p-tolyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 494582-69-3 5-(4-chloro-phenyl)-1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3-phenyl-tetrahydro-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 494583-22-1 1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3,5-diphenyl-3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 494583-27-6 5-(4-chloro-phenyl)-1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3-phenyl-3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 494583-33-4 1-(4-oxo-4,5-dihydro-thiazol-2-yl)-3-phenyl-5-p-tolyl-3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione 
• 7701-23-7 3-benzyl-2-(2-benzylidenehydrazono)thiazolidin-4-one 

Relevant articles and documents

Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase

Insect chitinase and N-acetyl-β-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R1 at N3) and II (with substituted group R1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R1, demonstrated the best inhibitory activities against OfHex1 and OfChi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (Ki = 1.5 μmol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (Ki = 5.9 μmol/L). The differences in compounds’ binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (Ki = 1.9 μmol/L) and II-3d (Ki = 4.1 μmol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors.

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.

Synthesis of bisthiazolo[3,4-b ; 3',2'-d]-1,2,4-triazol-8(3H, 7H)ones as potential herbicides

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