6318-37-2

Usage

InChI:InChI=1/C10H6ClNOS2/c11-7-3-1-6(2-4-7)5-8-9(13)12-10(14)15-8/h1-5H,(H,12,13,14)/b8-5-

Upstream product

• 98026-85-8 5-chloromethylene-2-thioxo-thiazolidin-4-one 
• 108-90-7 chlorobenzene 
• 104-88-1 4-chlorobenzaldehyde 
• 19374-88-0 5-(1-methyl-3-oxo-butylidene)-2-thioxo-thiazolidin-4-one 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 538-51-2 benzylidene phenylamine 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 

Downstream Products

• 65562-27-8 5-(4-chloro-benzylidene)-3-(tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 104183-58-6 5-(p-Chlorobenzylidene)-3--4-oxo-thiazolidine-2-thione 
• 104183-59-7 5-(p-Chlorobenzylidene)-3--4-oxo-thiazolidine-2-thione 
• 104183-57-5 5-(p-Chlorobenzylidene)-3--4-oxo-thiazolidine-2-thione 
• 23517-83-1 5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine 
• 76979-35-6 2-methylthio-5-p-chlorophenylmethylene-thiazolinone-4 
• 76988-00-6 5-(4-Chlorophenylmethylene)-2-imino-4-thiazolidinone 
• 36937-47-0 5-(4-Chlorophenylmethylene)-2-morpholino-4-oxo-2-thiazoline 
• 15788-48-4 5-(4-Chlorophenylmethylene)-2-piperidino-2-thiazolin-4-one 
• 99839-78-8 3-(4-chlorophenyl)propionic amide 

Relevant academic research and scientific papers

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.

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.]

Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors

Abstract A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative act

Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium

An efficient synthesis of 5 arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4- thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H2O-EtOH to afford the corresponding products in high yields at 50C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu4NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure(Equation presented). 2013

The chelating behaviour of 3-(4-X-phenyl)-2-sulfanylpropenoic acids with the PbII ion - Relevance of the lone electron pair in the supramolecular structures of the 2:1 complexes

The interaction of 3-(4-X-phenyl)-2-sulfanylpropenoic acids [H 2(X-pspa); X = -F, -Cl, -Br, -I, -OCH3, -OCF3, -OH] with lead(II) acetate in an alcoholic medium was explored in the search for new chelating agents for the Pb2+ ion. The direct reactions afforded [Pb(X-pspa)] complexes in yields of 67 (X = -Br) to 95 % (X = -OCH 3). When the PbII/H2(X-pspa) reaction was performed in the presence of diisopropylamine (Q), the derivatives [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) were obtained. All of the complexes were characterized by spectrometric (FAB-MS and ESI-MS) and spectroscopic (IR, 1H and 13C NMR spectroscopy) methods and these showed the permanence of the O,S coordination of the ligands to the metal ion in dimethyl sulfoxide (DMSO) solution. H2(Cl-pspa), [HQ]2[Pb(Cl-pspa)2] and [HQ]2[Pb(Br-pspa) 2] were also fully characterized in the solid state by X-ray diffraction. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) is discussed. The characteristics of complexes formed by 3-(4-X-phenyl)-2-sulfanylpropenoic acids with lead(II) cations have been explored both in the solid state and in solution. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br; Q = diisopropylamine) is discussed. Copyright

Facile and convenient synthesis of 5-arylalkylidenerhodanines by electrocatalytic crossed aldol condensation

An electrochemically induced catalytic crossed Aldol condensation of one equivalent of rhodanine with various aromatic aldehydes and ketones in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of th

Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones

An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.

A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid

2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.