Abstract
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.
Highlights
The 1,3-dipolar cycloaddition reactions [1] have been established as an efficient method for the construction of five-membered nitrogen heterocycles
The present study has been reported through a highly selective regio- and stereo-scopic cycloaddition reaction derived from acenaphthenequinone and sarcosine with several dipolaro files such as substituted 5-benzylidene-2-thioxothiazolidin-4-ones
Chemistry 5-benzylidene-2-thioxothiazolidin-4-ones were prepared from rhodanine and various substituted aromatic aldehydes according to the method previously reported [17]
Summary
The 1,3-dipolar cycloaddition reactions [1] have been established as an efficient method for the construction of five-membered nitrogen heterocycles These five-member heterocycles are very important due to their high regioselectivity and stereoselectivity. The spirooxindole ring systems are the central skeleton of numerous alkaloids and therapeutically important compounds. More serious diseases such as cancer are considered the second leading cause of death worldwide after cardiovascular diseases. In India, approximately 1 million new cases occur each year. Almost 80% of cases occur in low-income countries or developing countries This emphasizes that the incessant need to develop new classes of anticancer agents is an important and challenging goal in medical chemistry. The present study has been reported through a highly selective regio- and stereo-scopic cycloaddition reaction derived from acenaphthenequinone and sarcosine with several dipolaro files such as substituted 5-benzylidene-2-thioxothiazolidin-4-ones
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