Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, People’s Republic of China
Received: 7 January 2020 Accepted: 9 September 2020
A facile synthesis of dehydroepiandrosterones derived by C-16 spiro-pyrrolidine and their cytotoxic evaluation are reported. Seven derivatives, 3a–3g, were prepared by the [3 + 2] cycloaddition reaction of the 16-arylidene dehydroepiandrosterone and the azomethine ylide, where the azomethine ylide was generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and sarcosine. Their cytotoxicity was evaluated on brine shrimp assay and the bioactivities represented by LC50 values were found in the range of 6.19–27.2 µg/mL. Among them, the activities of 3d and 3g are the best, as manifested by LC50 values less than 10 µg/mL. All products were confirmed by NMR, HR MS and X-ray analysis.