Synthesis of C3/C1-Substituted Tetrahydroisoquinolines
AbstractA broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammada scoparia 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 β-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. View Full-Text
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Mihoubi, M.; Micale, N.; Scala, A.; Jarraya, R.M.; Bouaziz, A.; Schirmeister, T.; Risitano, F.; Piperno, A.; Grassi, G. Synthesis of C3/C1-Substituted Tetrahydroisoquinolines. Molecules 2015, 20, 14902-14914.
Mihoubi M, Micale N, Scala A, Jarraya RM, Bouaziz A, Schirmeister T, Risitano F, Piperno A, Grassi G. Synthesis of C3/C1-Substituted Tetrahydroisoquinolines. Molecules. 2015; 20(8):14902-14914.Chicago/Turabian Style
Mihoubi, Mohamed; Micale, Nicola; Scala, Angela; Jarraya, Raoudha M.; Bouaziz, Amira; Schirmeister, Tanja; Risitano, Francesco; Piperno, Anna; Grassi, Giovanni. 2015. "Synthesis of C3/C1-Substituted Tetrahydroisoquinolines." Molecules 20, no. 8: 14902-14914.