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Molecules 2015, 20(8), 14902-14914; doi:10.3390/molecules200814902

Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

1
Laboratoire de Chimie des Substances Naturelles UR/11-ES-74, Faculté des Sciences de Sfax, Université de Sfax, Route de l’aeroport, BP 1171, 3000 Sfax, Tunisia
2
Dipartimento di Scienze del Farmaco e Prodotti per la Salute, Università degli Studi di Messina, Viale Annunziata, 98168 Messina, Italy
3
Dipartimento di Scienze Chimiche, Università di Messina, Viale Ferdinando Stagno D’Alcontres 31, 98166 Messina, Italy
4
Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, D 55099 Mainz, Germany
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 22 July 2015 / Revised: 5 August 2015 / Accepted: 10 August 2015 / Published: 14 August 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [814 KB, uploaded 14 August 2015]   |  

Abstract

A 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 (1011) 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
Keywords: Bischler-Napieralski condensation; N-methylisosalsoline; nitroalkene; proteasome; tetrahydroisoquinoline Bischler-Napieralski condensation; N-methylisosalsoline; nitroalkene; proteasome; tetrahydroisoquinoline
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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