Abstract
Background4-Thiazolidinone ring is reported to have almost all types of biological activities. Also, it present in many marketed drugs.ResultsEthyl acetoacetate reacted with phenyl isothiocyanate and ethyl chloroacetate in presence of K2CO3 and DMF to afford the thiazolidinone derivative 5. Thiazolidinone 5 reacted with dimethylformamide-dimethylacetal to afford (Z)-ethyl 2-((Z)-5-((dimethylamino) methylene)-4-oxo-3-phenylthiazolidin-2-ylidene)acetate (6). The structure of thiazolidinone 6 was elucidated from its spectral analysis and X-ray crystallography and was optimized using B3LYP/6-31G(d,p) method. The geometric parameters and NMR spectra were discussed both experimentally and theoretically. Also, the natural charges at the different atomic sites were predicted. The synthesized compounds had moderate cytotoxic activity.ConclusionsAn unexpected synthesis of (Z)-ethyl 2-((Z)-5-((dimethylamino)methylene)-4-oxo-3-phenylthiazolidin-2-ylidene)acetate via deacetylation mechanism. The structure was established using X-ray and spectral analysis. The geometric parameters, and NMR spectra were discussed. The synthesized compounds showed moderate anticancer activity.
Highlights
The thiazolidinone ring had diverse biological activities such as antimycobacterial [1], antimicrobial [2], anticancer [3], anticonvulsant [4], antiparasitic [5], antidiabetic [6], and antihypertensive [7]
Chemistry The thiazolidinone derivative 5 was prepared according to the reported method [15]
The following reaction mechanism was suggested for the formation of thiazolidinone derivative 6 (Scheme 2)
Summary
Ethyl acetoacetate reacted with phenyl isothiocyanate and ethyl chloroacetate in presence of K 2CO3 and DMF to afford the thiazolidinone derivative 5.
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