51347-26-3

Upstream product

• 100-46-9 benzylamine 
• 103-72-0 phenyl isothiocyanate 
• 105-36-2 ethyl bromoacetate 
• 726-25-0 1-benzyl-3-phenylthiourea 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 

Downstream Products

• 51347-21-8 3-(3-benzyl-4-oxo-2-phenylimino-thiazolidin-5-ylidene)-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules

A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.

Synthesis of 2-iminothiazolidin-4-ones using guanine functionalized SBA-16 as a solid base catalyst

The first example of a one-pot three-component tandem annulation approach is described for the synthesis of 2-iminothiazolidin-4-ones by the reaction of aromatic/aliphatic amines, aryl isothiocyanates, and ethyl bromoacetate, catalysed by guanine-functionalized SBA-16, [SBA-16@G], as an efficient and recyclable heterogeneous solid base catalyst. The methodology is simple and offers a broad-substrate scope under mild reaction conditions.

Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents

Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.

Visible Light-Promoted Three-Component Tandem Annulation for the Synthesis of 2-Iminothiazolidin-4-ones

Described is a visible light-promoted three-component tandem annulation of amines, aryl/alkyl isothiocyanates, and α-bromoesters to form 2-iminothiazolidin-4-ones in the absence of metal and photocatalyst at room temperature. This [1 + 2 + 2] cyclization strategy involves visible light-promoted C-S/C-N bond formation and features a powerful approach to the synthesis of 2-iminothiazolidin-4-ones with broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation, which also has potential applications in the pharmaceutical industry. UV-vis spectroscopy indicates that an in situ-generated H-bonding electron donor-acceptor (EDA) complex probably acts as the photocatalyst, facilitating the reaction process.

Electrogenerated base-promoted synthesis and antimicrobial activity of 2-imino-1,3-thiazolidin-4-one derivatives

Electrogenerated cyanomethylanions obtained by reduction of dry acetonitrile at a steel grid cathode were used to promote the addition of ethyl bromoacetate to thiourea derivatives. The reaction yields the corresponding 2-imino-1,3-thiazolidin-4-one. The

Facile and regioselective synthesis of thiazolidin-4-one derivatives catalyzed by basic ionic liquid [bmim]OH under ultrasonic irradiation

2-Iminothiazolidin-4-one derivatives were synthesized regioselectively in good to high yields by condensation of N,N-disubstituted thioureas and ethyl chloroacetate in the presence of basic ionic liquid [bmim]OH as a catalyst under conventional and ultrasonic irradiation conditions. Under ultrasonic irradiation, the reaction furnished the desired 2-iminothiazolidinones in higher yields (76-87%) and lower reaction times (30-55 min).