453-69-0

Basic information

• Product Name: 3-(4-fluorobenzyl)-2-thioxo-1,3-thiazolidin-4-one
• CAS NO: 453-69-0
• Molecular Formula: C₁₀H₈FNOS₂
• Molecular Weight: 241.305
• Mol File: 453-69-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 358.2°C at 760 mmHg
• Flash Point: 170.5°C
• Density: 1.46g/cm³
• Vapor Pressure: 2.58E-05mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 3-(4-fluorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(453-69-0)
• EPA Substance Registry System: 3-(4-fluorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(453-69-0)

Safety Data

• Hazardous Substances Data: 453-69-0(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 79-11-8 chloroacetic acid 
• 140-75-0 para-fluorobenzylamine 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 1194-02-1 4-fluorobenzonitrile 
• 3926-62-3 sodium monochloroacetic acid 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 

Downstream Products

• 1277116-58-1 (Z)-4-(5-((3-(4-fluorobenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)-2-hydroxybenzoic acid 
• 784-79-2 3-(4-fluoro-benzyl)-2-thioxo-thiazolidine-4,5-dione 5-oxime 

Relevant articles and documents

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.

HETEROCYCLIC INTEGRIN AGONISTS

The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.

Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.