Efficient approach to thiazolidinones via a one-pot three-component reaction involving 2-amino-1-phenylethanone hydrochloride,aldehyde and mercaptoacetic acid

A highly efficient three-component reaction has been developed for the synthesis of thiazolidinones involving the reaction of 2-amino-l-phenylethanone hydrochloride with an aromatic aldehyde and mercaptoacetic acid in the presence of diisopropylethylamine in a single pot.Critically,this reaction exhibited excellent chemoselectivity,with the nitrogen atom of the 2-amino-l-phenylethanone component reacting selectively with the aromatic aldehyde to give the corresponding Schiff base.Nucleophilic attack at the carbon of the Schiff base by the sulfur atom of mercaptoacetic,followed by a cyclocondensation reaction between the nitrogen and the carboxylic acid moiety afforded the desired thiazolidinones,which were fully characterized by spectroscopic techniques.

Synthesis of Some New Spiro <i>β</i>-Lactams and Thiazolidinones Compounds Containing Sulfur Incorporating Quinon Compounds

A series of spiro, β-Lactams, and thiazolidinones incorporating compounds 4 have been synthesized by cycloaddition reaction of, chloroacetyl chloride and mercaptoacetic acid with the synthesized Shiff,s bases 5a-c to give new spiro β- Lactam 6a-c and spiro thiazolidinone 7a-c the cycloaddition were characterized by spectral data including HNMR, 13C-NMR, IR and elemental analysis.

A novel synthesized prodrug of gemcitabine based on oxygen-free radical sensitivity inhibited the growth of lung cancer cells

In the present study,we introduced the H2O2-sensitive thiazolidinone moiety at the 4th amino group of gemcitabine(GEM)to synthesize a new target compound named GEM-ZZQ,and then we confirmed its chemical structure by nuclear magnetic resonance spectroscopy.We further confirmed that GEM-ZZQ had a good chemical stability in different pH solutions in vitro and that it could be activated by H2O2 to release GEM.Pharmacodynamic studies revealed that the growth inhibition of human normal epithelial cells was weaker by GEM-ZZQ than by GEM treatment and that the inhibition of various lung cancer cell lines by GEM-ZZQ was similar to that of GEM.For the lung cancer cell lines that are resistant to the epidermal growth factor receptor(EGFR)-targeting inhibitor osimertinib,GEM-ZZQ showed less growth inhibition than GEM;however,GEM-ZZQ in combination with cisplatin showed better synergistic effects than GEM in the low-dose groups.In summary,we provided a new anti-cancer compound GEM-ZZQ for treating lung cancer by modifying the GEM structure.

Reaction of thiocarboxanilide derivatives of 2-phenylimino-3-phenyl-4-thiazolidinone and 1,3-diphenyl-2-thioxo-4-imidazolone with hydrazonoyl halides and active chloromethylene compounds

The potassium salts of thiocarboxanilide of 2- phenylimino-3-phenyl-4-thiazolidinone and 1,3- diphenyl-2-thioxo-4-imidazolone react with hydrazonoyl halides in N,N-dimethylformamide to afford the corresponding 1,3,4-thiadiazoline derivatives. 2-Phenylimino-3-phenyl-4-thiazolidinone reacts with active chloromethylene compounds in N,N-dimethylformamide to give the corresponding thiazolylidenethiazolidin-4-one derivatives. The new compounds were characterized using IR, 1H NMR, 13C NMR and mass spectra.