A novel synthesis, X-ray analysis and computational studies of (Z)-ethyl 2-((Z)-5-((dimethylamino)methylene)- 4-oxo-3-phenylthiazolidin-2-ylidene)acetate as a potential anticancer agent View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-12

AUTHORS

Yahia N. Mabkhot, Mohammed M. Alharbi, Salim. S. Al-Showiman, Saied M. Soliman, Nabila A. Kheder, Wolfgang Frey, Abdulrhman Asayari, Abdullatif Bin Muhsinah, H. Algarni

ABSTRACT

4-Thiazolidinone ring is reported to have almost all types of biological activities. Also, it present in many marketed drugs. Ethyl 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. An 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. More... »

PAGES

35

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1186/s13065-019-0554-2

DOI

http://dx.doi.org/10.1186/s13065-019-0554-2

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