Facile preparation and preliminary cytotoxicity evaluation of dehydroepiandrosterone C-16 spiro-pyrrolidine derivatives
| Autor: | Hongwen Tao, Lu-Yao Zeng, Pinggui Yi, Wen-Yu Peng, Jiang-Chun Yuan, Qiang Li, Xianyong Yu |
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| Rok vydání: | 2020 |
| Předmět: |
Sarcosine
Chemistry General Chemical Engineering Azomethine ylide Dehydroepiandrosterone 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Biochemistry Medicinal chemistry Industrial and Manufacturing Engineering Cycloaddition Pyrrolidine 0104 chemical sciences chemistry.chemical_compound Materials Chemistry 0210 nano-technology Cytotoxicity |
| Zdroj: | Chemical Papers. 75:823-829 |
| ISSN: | 1336-9075 2585-7290 |
| DOI: | 10.1007/s11696-020-01346-4 |
| Popis: | 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. Graphic abstract |
| Databáze: | OpenAIRE |
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