期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 20, 期 11, 页码 3666-3674出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2012.03.066
关键词
Lupane; Oleanane; Heterocycles; Cytotoxicity; Diazotization; Pyrazoles; Isoxazoles; Thiazoles; Triterpenes; Bromination
资金
- Czech Science Foundation [305/09/1216, 301/09/P433]
- Grant Agency of the CTU in Prague [SGS11/133/OHK4/2T/14]
- Operational Program Research and Development for Innovations [CZ. 1.05/2.1.00/01.0030]
- [MSM0021620857]
The aim of this work was to synthesize a set of heterocyclic derivatives of lupane, lup-20(29)-ene, and 18 alpha-oleanane, and to investigate their cytotoxic activities. Some of those heterocycles were previously known in the oleanane (allobetulin) group; however, to our knowledge the syntheses and biological activities of lupane heterocycles have not been reported before. Starting from betulin (1) and betulinic acid (2), we prepared 3-oxo compounds and 2-bromo-3-oxo compounds 3-10, 2-hydroxymethylene-3-oxo compounds 11-13 and beta-oxo esters 14-16. Condensation of these intermediates with hydrazine, phenylhydrazine, hydroxylamine, or thiourea yielded the pyrazole and phenylpyrazole derivatives 1722, pyrazolones 23-25, isoxazoles 26 and 27, and thiazoles 28-31. Fifteen compounds (14-16, 18-25, and 29-32) have not been reported before. The cytotoxicity was measured using panel of seven cancer cell lines with/without MDR phenotype and non tumor MRC-5 and BJ fibroblasts. The preferential cytotoxicity to cancer cell lines, particularly to hematological tumors was observed, the bromo acids 5, 6 showed highest activity and selectivity against tumor cells. (C) 2012 Elsevier Ltd. All rights reserved.
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