期刊
MOLECULES
卷 20, 期 8, 页码 14902-14914出版社
MDPI
DOI: 10.3390/molecules200814902
关键词
Bischler-Napieralski condensation; N-methylisosalsoline; nitroalkene; proteasome; tetrahydroisoquinoline
资金
- Ministero dell'Istruzione, dell'Universita e della Ricerca (MIUR) [PRIN20109Z2XRJ 010]
- Ministry of High Education and Scientific Research of Tunisia
- DFG (Deutsche Forschungsgemeinschaft) [SFB630]
A broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammadascoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10-11) with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for the condensation to the tetrahydroisoquinoline system, i.e., a functionalized -arylethyl amine, was obtained through an original double reduction of nitroalkene. The synthetic strategy can be directed to the construction of highly substituted and functionalized 1,2,3,4-tetrahydroisoquinolines.
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