23538-04-7

Basic information

• Product Name: 3-(4-chlorobenzyl)-2-thioxo-1,3-thiazolidin-4-one
• CAS NO: 23538-04-7
• Molecular Formula: C₁₀H₈ClNOS₂
• Molecular Weight: 257.7596
• Mol File: 23538-04-7.mol

Chemical Properties

• Boiling Point: 382.5°C at 760 mmHg
• Flash Point: 185.1°C
• Density: 1.5g/cm³
• Vapor Pressure: 4.71E-06mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: 3-(4-chlorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-chlorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(23538-04-7)
• EPA Substance Registry System: 3-(4-chlorobenzyl)-2-thioxo-1,3-thiazolidin-4-one(23538-04-7)

Safety Data

• Hazardous Substances Data: 23538-04-7(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 105-36-2 ethyl bromoacetate 
• 104-86-9 4-chlorobenzylamine 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 79-11-8 chloroacetic acid 

Downstream Products

• 27550-04-5 3-(4-chloro-benzyl)-5-(5-nitro-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one 
• 1277116-70-7 (Z)-4-(5-((3-(4-chlorobenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)-2-hydroxybenzoic acid 
• 91762-27-5 3-(4-chloro-benzyl)-5-(dimethylamino-methylene)-2-thioxo-thiazolidin-4-one 
• 34396-56-0 3-(4-chloro-benzyl)-2-thioxo-thiazolidine-4,5-dione 5-oxime 
• 97026-68-1 3-(4-chloro-benzyl)-5-ethoxymethylene-2-thioxo-thiazolidin-4-one 

Relevant articles and documents

ANTIVIRAL COMPOUNDS AND USE THEREOF

The present invention relates to compounds of formula (I), their use as medicaments, in particular as broad spectrum antiviral agents, their combination with a further antiviral agent and relative pharmaceutical compositions. In particular, the compounds of the invention are useful in the treatment of a disease caused by an enveloped virus.

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.

One drug for two targets: Biological evaluation of antiretroviral agents endowed with antiproliferative activity

AIDS-related cancer diseases are malignancies with low incidence on healthy people that affect mostly subjects already immunocompromised. The connection between HIV/AIDS and these cancers has not been established yet, but a weakened immune system is certa

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.

Aqueous microwave-assisted one-pot synthesis of N-substituted rhodanines

Two aqueous, one-pot, microwave-assisted methods for the rapid synthesis of N-substituted rhodanines from amine substrates are described. Alkyl- and benzylamines could be converted into the corresponding rhodanines with an atom-efficient one-pot, three-step protocol based on carbon disulfide and chloroacetic acid in short reaction times and good to excellent yields. An alternative, microwave-assisted one-pot, one-step protocol using bis(carboxymethyl)trithiocarbonate in water was developed for the synthesis of N-arylrhodanines from anilines.

A Versatile and Practical Synthesis toward the Development of Novel HIV-1 Integrase Inhibitors

As a continuation of our previous work, which resulted in the identification of a new hit compound as an HIV-1 integrase inhibitor, three novel series of salicylic acid derivatives were synthesized using three versatile and practical synthetic strategies and were assayed for their capacity to inhibit the catalytic activity of HIV-1 integrase. Biological evaluations revealed that some of the synthesized compounds possess good inhibitory potency in enzymatic assays and are able to inhibit viral replication in MT-4 cells at low micromolar concentrations. Finally, docking studies were conducted to analyze the binding mode of the synthesized compounds within the DNA binding site of integrase in order to refine their structure-activity relationships. Easy as A, B, C: Three new series of salicylic acid derivatives were designed and synthesized to investigate their activity toward HIV-1 integrase. Some of these compounds were obtained with microwave-assisted procedures developed and optimized in our research group, which allowed us to rapidly generate several final compounds of high purity.

Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives

Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochemical reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with ethyl 3-bromopropionate acid ester or with ethyl 2-bromoacetate acid ester yields the corresponding ring-opened carbamodithioate compounds or cyclic rhodanine derivatives, respectively. The effect of the amount of electrogenerated base on the yield of reaction was also evaluated.