39123-31-4

Usage

InChI:InChI=1/C6H9NOS2/c1-2-3-7-5(8)4-10-6(7)9/h2-4H2,1H3

Upstream product

• 107-10-8 propylamine 
• 75-15-0 carbon disulfide 
• 79-11-8 chloroacetic acid 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 

Downstream Products

• 93959-31-0 4-Hexyloxy-benzoic acid 4-[4-oxo-3-propyl-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-13-8 3-n-Propyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 
• 245095-98-1 3-propyl-5-benzylidenerhodanine 
• 245096-01-9 3-propyl-5-cinnamylidenerhodanine 
• 1277116-66-1 (Z)-2-hydroxy-4-(5-((4-oxo-3-propyl-2-thioxothiazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid 
• 3698-10-0 3-Propyl-5-<4-dimethylamino-benzyliden>-rhodanin 

Relevant academic research and scientific papers

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.