5740-34-1

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 29, p. 427, 1951 DOI: 10.1139/v51-051

InChI:InChI=1/C20H18N2O3/c1-12(23)13-8-9-19-18(11-13)16-6-3-7-17(16)20(21-19)14-4-2-5-15(10-14)22(24)25/h2-6,8-11,16-17,20-21H,7H2,1H3

Upstream product

• 5178-04-1 3-methyl-5-benzylidenerhodanine 
• 3806-42-6 5-benzylidene-2-thioxothiazolidin-4-one 
• 100727-15-9 3-Allyl-5-benzyliden-2-thioxothiazolidin-4-on 
• 622-29-7 N-Benzylidenemethylamine 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 100-52-7 benzaldehyde 
• 1151944-57-8 (Z)-2-(5-benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic acid 
• 3806-42-6 (Z)-5-benzylidene-2-thioxothiazolidin-4-one 
• 79788-56-0 5-(Methylamino-phenyl-methyl)-3-phenyl-2-thioxo-thiazolidin-4-one 

Downstream Products

• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 99033-95-1 2-hydroxyimino-3-phenylpropanoic acid 
• 72772-24-8 S(+)-2-mercapto-3-phenylpropionic acid 
• 93655-62-0 α,α'-disulfanediyl-di-cinnamic acid 
• 42056-21-3 5-benzylidene-3-(4-chloro-phenyl)-2-phenyl-thiazolidin-4-one 
• 42056-22-4 5-benzylidene-3-(4-bromo-phenyl)-2-phenyl-thiazolidin-4-one 
• 104484-26-6 3-benzylidene-6-ethoxycarbonyl-1,4-oxathiin-2(3H)-one 
• 104484-36-8 (E)-2-(1-Ethoxycarbonyl-2-oxo-2-phenyl-ethylsulfanyl)-3-phenyl-acrylic acid 
• 104484-08-4 α-acetylthio-β-phenylacrylic acid 
• 104484-30-2 (Z)-2-(2-Oxo-propylsulfanyl)-3-phenyl-acrylic acid 
• 79878-53-8 5-benzylidene-2-ethoxycarbonylmethyl-2-thiazolin-4-one 
• 104484-29-9 α-(2-oxo-2-phenylethylthio)-β-phenylacrylic acid 
• 79421-53-7 2-Cyanomethyl-5-benzylidene-2-thiazolin-4-one 
• 104484-33-5 α-(1-ethoxycarbonyl-2-oxopropylthio)-β-phenylacrylic acid 

Relevant academic research and scientific papers

Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases

Metallo-β-lactamases (MBLs) enable bacterial resistance to almost all classes of β-lactam antibiotics. We report studies on enethiol containing MBL inhibitors, which were prepared by rhodanine hydrolysis. The enethiols inhibit MBLs from different subclasses. Crystallographic analyses reveal that the enethiol sulphur displaces the di-Zn(II) ion bridging ‘hydrolytic’ water. In some, but not all, cases biophysical analyses provide evidence that rhodanine/enethiol inhibition involves formation of a ternary MBL enethiol rhodanine complex. The results demonstrate how low molecular weight active site Zn(II) chelating compounds can inhibit a range of clinically relevant MBLs and provide additional evidence for the potential of rhodanines to be hydrolysed to potent inhibitors of MBL protein fold and, maybe, other metallo-enzymes, perhaps contributing to the complex biological effects of rhodanines. The results imply that any medicinal chemistry studies employing rhodanines (and related scaffolds) as inhibitors should as a matter of course include testing of their hydrolysis products.

Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates

Reaction of NaAuCl4H2O and thiodiglycol (1:3 molar ratio) with 3-(aryl)-2-sulfanylpropenoic acids, H2xspa0[x:p03-phenyl- , f03-(2-furyl)-, t03-(2-thienyl)-, o-py03-(2-pyridyl)-, Clp03-(2-chlorophenyl)- , -o-mp03- (2-methox

Versatile routes to marine sponge metabolites through benzylidene rhodanines

The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimizatio

Palladium-catalysed direct synthesis of benzo[b]thiophenes from thioenols

The one-pot conversion of thioenols into benzo[b]thiophenes was achieved by using a simple palladium catalyst such as PdCl2 or PdCl 2(cod). The Royal Society of Chemistry.

New structural features in triphenylphosphinesilver(I) sulfanylcarboxylates

We investigated the reactions of 1.5 : 1 : 1 mole ratio mixtures of triphenylphosphine, silver nitrate and 3-(aryl)-2-sulfanylpropenoic acids H 2xspa in chloroform/water, where in the acid nomenclature, spa = 2-sulfanylpropenoato and x = p, Clp

POTASSIUM FLUORIDE ON ALUMINA: CONDENSATION OF 3-METHYL-2-THIONO-4-THIAZOLIDINONE WITH ALDEHYDES. SYNTHESIS OF α-THIOACRYLIC ACIDS AND PHOSPHONOTHIONOTHIAZOLIDINONES

3-Methyl-2-thiono-4-thiazolidinone and aromatic aldehydes adsorbed on potassium fluoride on alumina gave under microwave irradiation 5-arylidene-3-methyl-2-thiono-4-thiazolidinones in 70percent to 90percent yield.These compounds can be cleaved with sodium

ADDITION OF HETEROCYCLIC CH ACIDS TO THE C=N BOND OF AZOMETHINES

The aminomethylation of oxindole, 1-phenyl-3-methyl-5-pyrazolone, and N-phenylrhodanine was studied.Derivatives of these CH acids were obtained as a result of aminomethylation.The addition products were subjected to acid and base hydrolysis; the correspon