3889-20-1

Basic information

• Product Name: 3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one
• Synonyms: 3-(2-Phenylethyl)-2-thioxo-1,3-thiazolidin-4-one; 3-phenethyl-2-thioxo-1,3-thiazolan-4-one; 4-Thiazolidinone, 3-(2-phenylethyl)-2-thioxo-
• CAS NO: 3889-20-1
• Molecular Formula: C₁₁H₁₁NOS₂
• Molecular Weight: 237.3411
• Mol File: 3889-20-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 369°C at 760 mmHg
• Flash Point: 176.9°C
• Density: 1.34g/cm³
• Vapor Pressure: 1.23E-05mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one(3889-20-1)
• EPA Substance Registry System: 3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one(3889-20-1)

Safety Data

• Hazardous Substances Data: 3889-20-1(Hazardous Substances Data)

Upstream product

• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 64-04-0 phenethylamine 
• 75-15-0 carbon disulfide 
• 79-11-8 chloroacetic acid 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 60-12-8 2-phenylethanol 
• 103-63-9 1-phenyl-2-bromoethane 
• 19457-11-5 phenethyl-dithiocarbamic acid 
• 79-08-3 bromoacetic acid 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 38427-90-6 N-(t-butoxycarbonyl)phenethylamine 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 32729-81-0 5-(5-nitro-furan-2-ylmethylene)-3-phenethyl-2-thioxo-thiazolidin-4-one 
• 1262518-99-9 2-chloro-3-{5-[4-oxo-3-phenethyl-2-thioxothiazolidin-5-ylidenemethyl]furan-2-yl}benzoic acid 
• 1262519-00-5 2-fluoro-3-{5-[4-oxo-3-phenethyl-2-thioxothiazolidin-5-ylidenemethyl]furan-2-yl}benzoic acid 
• 1204757-10-7 (Z)-3-phenethyl-5-((pyridin-3-yl)methylene)-2-thioxothiazolidin-4-one 
• 851303-33-8 (Z)-5-((furan-2-yl)methylene)-3-phenethyl-2-thioxothiazolidin-4-one 
• 1204757-12-9 (Z)-5-(3-bromobenzylidene)-3-phenethyl-2-thioxothiazolidin-4-one 
• 1204757-11-8 (Z)-5-((naphthalen-3-yl)methylene)-3-phenethyl-2-thioxothiazolidin-4-one 
• 1204757-09-4 (Z)-5-(3-methoxybenzylidene)-3-phenethyl-2-thioxothiazolidin-4-one 

Relevant articles and documents

Synthesis and biological evaluation of novel rhodanine-based structures with antiviral activity towards HHV-6 virus

An increased awareness of diseases associated with Human herpesvirus 6 (HHV-6) infection or reactivation has resulted in a growing interest in the evaluation of the best treatment options available for the clinical management of HHV-6 disease. However, no

A concise approach to n-substituted rhodanines through a base-assisted one-pot coupling and cyclization process

An efficient approach to obtain functionalized rhodanines was developed through a base-assisted one-pot coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate. This conversion tolerates a broad range of functional groups and can be used to scale the preparation of N-substituted rhodanines in excellent yields.

Small molecule fusion inhibitors: Design, synthesis and biological evaluation of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3- carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives targeting HIV-1 gp41

By a scaffold elongation strategy, a series of (Z)-3-(5-(3-benzyl-4-oxo-2- thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2, 5-dimethylpyrroles and related derivatives with a linear multi-aromatic-ring skeleton were designed, synthesized, and evaluated in HIV-1 gp41 and cellular assays. Among them, the most active compounds, 12e, 12g, and 12k with a one-carbon linker (n = 1) between the rhodanine (C) and phenyl (D) rings, exhibited very promising inhibitory potency with IC50 values of 1.8-2.6 μM and EC50 values of 0.3-1.5 μM against gp41 6-HB formation and HIV-1 replication in MT-2 cells, respectively. Additionally, they were almost equally effective against both T20-sensitive and resistant strains. The related SAR studies and molecular modeling results provided potential for further developing a new class of non-peptide small molecular fusion inhibitors targeting the HIV-1 gp41.