1457-47-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Allylrhodanine is used as an active pharmaceutical ingredient for its anticonvulsive properties, helping in the treatment of various conditions related to seizures and convulsions.
Used in Photography Industry:
3-Allylrhodanine is used as an intermediate in the synthesis of sensitizers for silver halide photographic emissions, enhancing the sensitivity and quality of photographic films and papers.
Used in Chemical Synthesis:
3-Allylrhodanine serves as a valuable intermediate in the synthesis of various other chemical compounds, contributing to the development of new materials and products in different industries.

InChI:InChI=1/C6H7NOS2/c1-2-3-7-5(8)4-10-6(7)9/h2H,1,3-4H2

Upstream product

• 68-11-1 mercaptoacetic acid 
• 57-06-7 N-allyl isothiocyanate 
• 4438-95-3 thiocyanato-acetic acid 
• 2365-48-2 Methyl thioglycolate 
• 107-11-9 1-amino-2-propene 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 75-15-0 carbon disulfide 
• 79-11-8 chloroacetic acid 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 40135-33-9 sodium allylcarbamodithioate 
• 105-39-5 chloroacetic acid ethyl ester 
• 3926-62-3 sodium monochloroacetic acid 

Downstream Products

• 115121-58-9 3-allyl-5-[2-(3-methyl-3H-benzothiazol-2-ylidene)-1-phenyl-ethylidene]-2-thioxo-thiazolidin-4-one 
• 5243-66-3 3-allyl-5-pyridin-2-ylmethylene-2-thioxo-thiazolidin-4-one 
• 104397-15-1 4-[(3-ethyl-4,5-diphenyl-3H-oxazol-2-yliden)-ethyliden]-2-[(3-allyl-4-oxo-2-thioxo-thiazolidin-5-yliden)-ethylidene]-3-methyl-thiazolidin-5-one 
• 1367579-16-5 3-allyl-5-(3,5-dichlorobenzylidene)-2-thioxothiazolidin-4-one 
• 1367579-20-1 3-allyl-5-(4-{3-dimethylaminopropoxy}benzylidene)-2-thioxothiazolidin-4-one 
• 309936-56-9 3-allyl-5-(4-bromobenzylidene)-2-thioxothiazolidin-4-one 
• 890996-21-1 3-allyl-5-(4-phenylbenzylidene)-2-thioxothiazolidin-4-one 
• 3730-51-6 3,3'-diallyl-5-(4-hydroxy-benzylidene)-2'-thioxo-dihydro-[2,5']bithiazolylidene-4,4'-dione 

Relevant academic research and scientific papers

Synthesis of 2-sulfanylidene-1,3-thiazolidin-4-one derivatives

Three-component condensation of primary amines with carbon disulfide and dialkyl maleates afforded the corresponding alkyl (3-R-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl)acetates whose structure was confirmed by independent synthesis and IR and 1/s

Synthesis and evaluation of some novel N-substituted rhodanines for their anticancer activity

Novel N-substituted rhodanines 2a-g were synthesized by conventional and microwave-assisted methods and tested for their anticancer activity. Structure-activity relationship of the synthesized rhodanine 2a-g as antiproliferative agents was investigated. The results revealed that all the seven compounds showed potent antiproliferative activity in a concentration-dependent manner on leukemic cell line K562. Among the tested compounds, 2b was found to be more potent when compared by trypan blue and MTT assay. IC50 values of 2b using trypan blue and MTT assay were found to be 11.1 and 20.3 μg/ml, respectively. A dose-dependent increase in the LDH release was also observed upon treatment with 2a-g. Cell cycle analysis revealed that 2b affects DNA replication and leads to accumulation of cells in G0 and decline of G2/M, G1 and S phases which indicates apoptosis. The selective cytotoxic activity against human chronic myelogenous cell line (K562), via apoptosis, suggests that compound 2b is a promising scaffold for the development of novel anticancer drug.

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.

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.

Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors

We have previously reported the discovery of a new class of potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) derived from benzylidene oxazolidinedione and thiazolidinedione scaffolds. In this study, these analogs were designed, synthesized, and evaluated in a human cell-based assay. The detailed structure-activity relationship (SAR) surrounding this pharmacophore were developed, and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg, 16 showed approximately two times more potent testosterone (T)-lowering effect against a positive control in the luteinizing hormone-releasing hormone (LH-RH)-induced T production assay. The T-lowering effect continued at ca 10% level of control over 4 h after administration. The nonsteroidal molecules based on this series have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer.

A convenient synthesis of N-substituted 2-thioxo-1,3-thiazolidin-4-ones

A convenient method was developed for the synthesis of N-substituted rhodanines based on the reaction of amines, hydrazides, or acid thiohydrazides with trithiocarbonyl diglycolic acid in the presence of dicyclohexylcarbodiimide or 1,1′-carbonyldiimidazole. Georg Thieme Verlag Stuttgart.

Arylalkylidene rhodanine with bulky and hydrophobic functional group as selective HCV NS3 protease inhibitor

Arylalkylidene rhodanines 2(a-d) inhibit HCV NS3 protease at moderate concentrations. They are better inhibitors of other serine proteases such as chymotrypsin and plasmin. However, the selectivity of arylmethylidene rhodanines (8a, 9a) with bulkier and more hydrophobic functional groups increases by 13- and 25-fold towards HCV NS3 protease respectively.