Mabkhot Yahia N, Alharbi Mohammed M, Al-Showiman Salim S, Soliman Saied M, Kheder Nabila A, Frey Wolfgang, Asayari Abdulrhman, Bin Muhsinah Abdullatif, Algarni H
1Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha, 61441 Saudi Arabia.
2Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451 Saudi Arabia.
BMC Chem. 2019 Mar 26;13(1):35. doi: 10.1186/s13065-019-0554-2. eCollection 2019 Dec.
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 KCO and DMF to afford the thiazolidinone derivative . Thiazolidinone reacted with dimethylformamide-dimethylacetal to afford (Z)-ethyl 2-((Z)-5-((dimethylamino) methylene)-4-oxo-3-phenylthiazolidin-2-ylidene)acetate (). The structure of thiazolidinone 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.
据报道，4-噻唑烷酮环具有几乎所有类型的生物活性。此外，它存在于许多市售药物中。
乙酰乙酸乙酯在碳酸钾和N,N-二甲基甲酰胺存在下与异硫氰酸苯酯和氯乙酸乙酯反应，得到噻唑烷酮衍生物。噻唑烷酮与N,N-二甲基甲酰胺-二甲基缩醛反应，得到(Z)-2-((Z)-5-((二甲基氨基)亚甲基)-4-氧代-3-苯基噻唑烷-2-亚基)乙酸乙酯()。通过光谱分析和X射线晶体学对噻唑烷酮的结构进行了阐明，并使用B3LYP/6-31G(d,p)方法进行了优化。对几何参数和核磁共振谱进行了实验和理论讨论。此外，还预测了不同原子位点的自然电荷。合成的化合物具有中等的细胞毒性活性。
通过脱乙酰化机制意外合成了(Z)-2-((Z)-5-((二甲基氨基)亚甲基)-4-氧代-3-苯基噻唑烷-2-亚基)乙酸乙酯。通过X射线和光谱分析确定了结构。对几何参数和核磁共振谱进行了讨论。合成的化合物显示出中等的抗癌活性。
