5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry.

A new domino-Knoevenagel–hetero-Diels–Alder reaction

Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives.

rel-(5aR,11bR)-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano[2,3-d][1,3]thiazol-2-ones formed by the stereoselective Knoevenagel-hetero-Diels-Alder reaction were functionalized at the nitrogen in position 3 via reactions of alkylation, cyanoethylation, and acylation. The synthesized compounds were evaluated for their anticancer activity in NCI60 cell lines. Among the tested compounds, 3f was found to be the most active candidate with the greatest influence on leukemia, non-small cell lung cancer, colon cancer, CNS cancer, melanoma, prostate cancer, and breast cancer subpanel cell lines with GI(50) values over a range of 0.37-0.67 μM.

https://www.mdpi.com/2218-0532/80/3/509/pdf

Fused Thiopyrano[2,3-d]thiazole Derivatives as Potential Anticancer Agents.

This review presents the up to date development of fused thiopyranothiazoles that comprise one of the thiazolidine derivatives classes. Thiazolidine and thiazolidinone-related compounds belong to the widely studied heterocycles from a medicinal chemistry perspective. From the chemical point of view, they are perfect heterodienes to undergo hetero-Diels–Alder reaction with a variety of dienophiles, yielding regio- and diastereoselectively thiopyranothiazole scaffolds. The annealing of thiazole and thiopyran cycles in condensed heterosystem is a precondition for the “centers conservative” creation of the ligand-target binding complex and can promote a potential selectivity to biotargets. The review covers possible therapeutic applications of thiopyrano[2,3-d]thiazoles, such as anti-inflammatory, antibacterial, anticancer as well as aniparasitic activities. Thus, thiopyrano[2,3-d]thiazoles may be used as powerful tools in the development of biologically active agents and drug-like molecules.

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Thiopyrano[2,3- d ]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry.

The 5-(ethoxymethylene)-4-thioxothiazolidin-2-ones 2a-c were synthesized and reacted with acrylonitrile, ethyl acrylate. β-nitrostyrene, N-phenylmaleimide and malononitrile under different conditions, to yield the cycloaddition products 3–14. The antibacterial and antifungal activities of the new products were tested.



Reaktionen mit 5-Ethoxymethylenthiazolidin-2,4-dion-Derivaten und ihre biologische Wirksamkeit



Die 5-Ethoxymethylen-4-thioxo-2-one 2a-c wurden synthetisiert und mit Acrylnitril, Ethylacrylat, β-Nitrostyrol, N-Phenylmaleinsaureimid und Malonodinitril unter verschiedenen Bedingungen umgesetzt. Die Wirkungen der neuen Verbindungen gegen Bakterien und Pilze wurde gepruft.

Yosry E. Saleh

Papers

5-(Ethoxymethylene)thiazolidine-2,4-dione derivatives: reactions and biological activities.

5-(Ethoxymethylene)thiazolidine-2,4-dione Derivatives: Reactions and Biological Activities.