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The thiazolidinone derivative 5 was prepared as described in the literature. The biological evaluations of the products were carried out in the Medical Mycology Laboratory of the Regional Center for Mycology and Biotechnology of Al-Azhar University, Cairo, Egypt.
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The single-crystal X-ray diffraction measurements were accomplished on a Bruker SMART APEX II CCD diffractometer. Elemental analysis were carried out on a 2400 CHN Elemental Analyzer. Chemical shifts δ are expressed in ppm units. Chemical shifts were related to that of the solvent. 1H spectra were run at 500 MHz and 13C spectra were run at 125 MHz in deuterated chloroform (CDCl 3). 1H- and 13C-NMR spectra were recorded on a JEOL ECP 500 NMR spectrometer operating at 500 MHz. The IR Spectra were recorded using Nicolet 6700 FT-IR spectrophotometer. The results revealed that thiazolidinone derivatives 5 and 6 had moderate anticancer activity against colon carcinoma (HCT-116).Īll the melting points were measured on a Gallenkamp apparatus in open glass capillaries and are uncorrected. The results of the cytotoxic activity were expressed as the mean IC 50 of three independent experiments (Table 6). The anti-cancer activity of the thiazolidine derivatives 5 and 6 was determined against the colon carcinoma (HCT-116) cell line in comparison with the anticancer drug vinblastine, using MTT assay. Since the oxygen and nitrogen atoms are more electronegative than carbons so the C-atoms (C4, C9, C12, and C20) attached to these electronegative sites were detected at high chemical shifts (162.4–177.4 ppm) compared to the rest of C-atoms. The high chemical shift of C30 is due to the deshielding effect of the electronegative N-atom. The atom C30 has higher chemical shift than the other aromatic carbons (Table 5). The chemical shifts of the aromatic carbons usually appear in the overlapped region of the spectrum between 100 and 200 ppm. The synthesized compounds showed moderate anticancer activity. The geometric parameters, and NMR spectra were discussed. The structure was established using X-ray and spectral analysis.
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ConclusionsĪn unexpected synthesis of (Z)-ethyl 2-((Z)-5-((dimethylamino)methylene)-4-oxo-3-phenylthiazolidin-2-ylidene)acetate via deacetylation mechanism. The synthesized compounds had moderate cytotoxic activity. Also, the natural charges at the different atomic sites were predicted. The geometric parameters and NMR spectra were discussed both experimentally and theoretically. 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. Thiazolidinone 5 reacted with dimethylformamide-dimethylacetal to afford (Z)-ethyl 2-((Z)-5-((dimethylamino) methylene)-4-oxo-3-phenylthiazolidin-2-ylidene)acetate ( 6).
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ResultsĮthyl acetoacetate reacted with phenyl isothiocyanate and ethyl chloroacetate in presence of K 2CO 3 and DMF to afford the thiazolidinone derivative 5. 4-Thiazolidinone ring is reported to have almost all types of biological activities.