387-27-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 384, 1956 DOI: 10.1021/ja01583a037

InChI:InChI=1/C9H6FNOS2/c10-6-1-3-7(4-2-6)11-8(12)5-14-9(11)13/h1-4H,5H2

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 352-34-1 4-fluoro-1-iodobenzene 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 1198159-34-0 (Z)-3-(4-fluorophenyl)-5-(3-ethoxy-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one 
• 1427538-23-5 (5Z)-5-{[5-(3,4-dichlorophenyl)-2-furyl]methylene}-3-(4-fluorophenyl)-2-thioxo-1,3-thiazolidin-4-one 

Relevant academic research and scientific papers

Quinolinone compound and application thereof

The invention discloses a quinolinone compound containing rhodanine and similar fragments thereof and pharmaceutically acceptable salts thereof, and relates to the technical field of organic chemistry. The quinolinone compound is shown as general formula I in the specification, wherein substituent groups R1, X and R2 have meanings given in the specification. The invention also relates to application of the compound shown as the general formula I and the pharmaceutically acceptable salts thereof in preparing medicines for treating diseases caused by abnormal expression of IDO, in particular toapplication in preparing medicines for treating and/or preventing cancers.

2-thiothiazolidine-4-one, derivative and preparation method thereof

The invention provides 2-thiothiazolidine-4-one, a derivative and preparation method thereof. Mercaptoacetic acid and thiourea are heated to synthesize 2-thiothiazolidine-4-one by taking 95% concentrated sulfuric acid as a catalyst. Under catalysis of active copper, 2-thiothiazolidine-4-one and halohydrocarbon are subjected to thin-layer chromatographic monitoring reaction through microwave irradiation by taking water as a solvent; solid is filtered after reaction is ended, is extracted by ethyl acetate, is dried, evaporated and dissolved to obtain a crude product which is subjected to columnchromatography isolation to obtain a rhodanine substitute; by taking piperidine as a catalyst, rhodanine substitute and aromatic formaldehyde react at the room temperature or under the reflux condition by taking dichloromethane or absolute ethyl alcohol as a solvent; and the reaction system is filtered while hot after reaction is ended to obtain the derivative of 2-thiothiazolidine-4-one. The synthesis route and equipment is simple, operations are simple, raw materials are cheap, the yield is high, the cost is reduced, economic benefits are improved, and is suitable for industrialized production.

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.

INHIBITORS OF BACTERIAL BIOFILM FORMATION

Organic compounds are described for use in inhibiting or preventing formation of bacterial biofilms.