81154-16-7

Usage

InChI:InChI=1/C11H9NO2S2/c1-14-8-4-2-7(3-5-8)6-9-10(13)12-11(15)16-9/h2-6H,1H3,(H,12,13,15)/b9-6+

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 123-11-5 4-methoxy-benzaldehyde 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 538-51-2 benzylidene phenylamine 
• 244032-72-2 [1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-thiourea 

Downstream Products

• 93515-30-1 3-(4-methoxyphenyl)-2-sulfanylpropenoic acid 
• 25413-27-8 3-(4-methoxy-phenyl)propionamide 
• 28996-11-4 5-(4-methoxy-benzylidene)-2-methylsulfanyl-thiazol-4-one 
• 28996-49-8 5-(4-methoxyphenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine 
• 68142-27-8 5-(4-methoxy-benzylidene)-2-thioxo-3-(2,4,6-trinitro-phenyl)-thiazolidin-4-one 
• 68142-30-3 3-(5-chloro-2,4-dinitro-phenyl)-5-(4-methoxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 68142-31-4 3-(4-chloro-2,6-dinitro-phenyl)-5-(4-methoxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 68142-35-8 5-(4-methoxy-benzylidene)-3-(3-methyl-2,4,6-trinitro-phenyl)-2-thioxo-thiazolidin-4-one 
• 68142-29-0 3-(2-bromo-4,6-dinitro-phenyl)-5-(4-methoxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 68142-34-7 5-(4-methoxy-benzylidene)-3-(4-methyl-2,6-dinitro-phenyl)-2-thioxo-thiazolidin-4-one 
• 76979-40-3 (Z)-5-(4-methoxybenzylidene)-2-(p-tolylamino)thiazol-4(5H)-one 
• 14837-03-7 Ag⁽¹⁺⁾*C₁₁H₈NO₂S₂^(1-)={AgC₁₁H₈NO₂S₂} 
• 92315-63-4 2-mercapto-3-(4-methoxy-phenyl)-propionic acid 
• 6320-51-0 (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis, molecular modeling, selective aldose reductase inhibition and hypoglycemic activity of novel meglitinides

In the present study, a novel generation of selective aldose reductase ALR2 inhibitors with significant hypoglycemic activities was designed and modulated based on rhodanine scaffold joined to an acetamide linker in between two lipophilic moieties. The synthesis of the novel compounds was accomplished throughout simple chemical pathways. Molecular docking was performed on B-cell membrane protein SUR1, aldehyde reductase ALR1 and aldose reductase ALR2 active sites. Compounds 10B, 11B, 12B, 15C, 16C, 26F and 27F displayed the highest hypoglycemic activities with 80.7, 85.2, 87, 82.3, 83.5, 81.4 and 85.3% reduction in blood glucose levels, respectively. They were more potent than the standard hypoglycemic agent repaglinide with 65.4% reduction in blood glucose level. Compounds 12B and 15C with IC50 0.29 and 0.35 μM were more potent than the standard ALR2 inhibitor epalrestat with IC50 0.40 μM. They were selective towards ALR2 over ALR1 134 and 116 folds, respectively. Molecular docking studies matched with the in-vitro and in-vivo results to elucidate the dual activities of both compounds 12B and 15C as potent antagonists for ALR2 over ALR1 and good agonists for the SUR1 protein.

Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative

A simple, efficient and environment-friendly procedure for the synthesis of 5-arylidene rhodanines derivatives via a Knoevenagel type reaction was developed using rhodanine, a variety of differently substituted aldehydes and Na2SO3 a

Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase

Dihydrodipicolinate synthase (DHDPS), responsible for the first committed step of the diaminopimelate pathway for lysine biosynthesis, has become an attractive target for the development of new antibacterial and herbicidal agents. Herein, we report the di

New N-ribosides and N-mannosides of rhodanine derivatives with anticancer activity on leukemia cell line: Design, synthesis, DFT and molecular modelling studies

N-ribosylation and N-mannosylation compounds have a great role in compounds activity as anticancer. The reaction of 2-thioxo-4-thiazolidinone (rhodanine) derivatives, as aglycon part, was done with ribofuranose and mannopyranose sugars (glycone part) foll

Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase

Broadened antibacterial activity was introduced to rhodanine derivatives targeting Mycobacterial tuberculosis enoyl-acyl carrier protein reductase (Mtb InhA) by recruiting feature of xacins to bring DNA Gyrase B inhibitory capability. This is significant for preventing further bacterial injections in the tuberculosis treatment. The most potent compound Cy14 suggested comparable bioactivity (IC50=3.18μM for Mtb InhA; IC50=10nM for DNA Gyrase B) with positive controls. Structure–activity relationship discussion and molecular docking model revealed the significance of rhodanine moiety and derived methoxyl on meta-position, pointing out orientations for future modification.

Discovery and development of novel rhodanine derivatives targeting enoyl-acyl carrier protein reductase

A series of rhodanine derivatives RB1–RB23 were synthesized through a two-round screening. Their Mycobacterial tuberculosis (Mtb) InhA inhibitory activity and Mtb growth blocking capability were evaluated. The most potent hit compound RB23 indicated compa

Synthesis, in-vitro cytotoxicity and antimicrobial evaluations of some novel thiazole based heterocycles

Condensation of rhodanine (1) with pyrazol-3(2H)-one derivatives (2a-f) gave 5-substituted-2-thioxo-1,3- thiazolidin-4-one derivatives (3a-f). Reaction of compound (1) with 2-arylmethylidene-malononitrile (4a-d) yielded the unexpected derivatives (5a-d). The latter compounds were subjected to cyclization reactions with malononitrile under different basic conditions, hydroxylamine hydrochloride and/or thiourea to furnish the fused thiazole derivatives (6a-d) and (8-10a-d). Coupling of (1) with diazotized aromatic amines (11a-c) in pyridine afforded the arylhydrazones (12a-c). Fusion of latter compounds with malononitrile afforded the thiazolopyridazine derivatives (13a-c). The structures of the newly synthesized compounds were elucidated via spectral data and elemental analyses. The in-vitro cytotoxic activity of compounds (3a-f) against the cell line MCF-7 was evaluated. Also, the synthesized products were investigated for their antibacterial and antifungal activities against six standard organisms including the G- bacteria, Staphylococcus aureus and Bacillus subtilis, G+ bacteria, Escherichia coli and Proteus vulgaris in addition to fungi, Candida albicans and Aspergillus flavus.

Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium

Abstract: TS-1 zeolite was prepared for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium by incorporating titanium(IV) cations in a silicate-1 framework using hydrothermal treatment and characterized by using XRD, EDX, BET, FT-IR and SEM techniques. The catalytic activity of the catalyst was tested for Knoevenagel condensation reaction. The condensation of active ethylene 2,4-thiazolidinedione with substituted aryl aldehydes under aqueous medium at 90?°C afforded the corresponding product in excellent yield up to 92% within 30?min. The present method offers several advantages over the reported methods such as easy separation of catalyst, simple work-up procedure, and an excellent yield of desired product. Furthermore, the catalyst could be reused without significant loss in activity. Graphical abstract: [Figure not available: see fulltext.]

HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY

The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used

Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents

Twenty novel 2-thioxo-1, 3-thiazolidin-4-one derivatives (5a-5t) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a. All the synthesized compounds were screened for their in-vitro antimycobacterial activity against MTB (H37RV, ATCC No: 27294) by Alamar Blue assay method. Compounds 5r, 5k, 5t displayed most potent in-vitro activity with MICs of 0.05, 0.1, 0.2 μg/ml concentrations respectively which are comparatively potent than the standards. Molecular docking and dynamics simulations were performed to find out the plausible mechanism of the titled compounds.