SYNTHESIS, SPECTRAL CHARACTERIZATION, AND ANTIPROLIFERATIVE ACTIVITY OF DISPIROPYRROLIDINES CONTAINING 2-THIOXOTHIAZOLIDIN-4-ONE NUCLEUS
Objective: Spiro compounds are present in nature, endowed with deep biological activities. Heterocyclic compounds with a pyrrolidine scaffold are one of the paradigms of organic chemistry that exhibits a wide variety of properties and biological functions. Based on these, seven dispiropyrrolidines have been accomplished by [3+2] cycloaddition reaction from acenaphthenequinone and sarcosine with several dipolaro files such as substituted 5-benzylidene-2-thioxothiazolidin-4-ones.
Methods: Cycloadducts 4a-g were prepared by conventional method and the structures of the compounds 4a-g were completely characterized by infrared, 1H, 13C nuclear magnetic resonance spectral data, and elemental analysis. The cytotoxic activity of the synthesized compounds was carried out by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay.
Results: The dispiropyrrolidines 4a-g were showed a moderate-to-good cytotoxic activity against human cervical cancer lines. Among all the synthesized compounds, 4d was found to be more potent with human cervical cancer line with an half maximal inhibitory concentration (IC50) value of 5.5 μM.
Conclusion: The synthesized compound 4d found to be an excellent activity which is nearly closed to reference drug gemcitabine with an IC50 value of 4.6 μM.
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