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Issue 27, 2013
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Discovery of new heterocycles with activity against human neutrophile elastase based on a boron promoted one-pot assembly reaction

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Abstract

Herein we demonstrate for the first time that a boron promoted one-pot assembly reaction may be used to discover novel enzyme inhibitors. Inhibitors for HNE were simply assembled in excellent yields, high diastereoselectivities and IC50 up to 1.10 μM, based on components like salicylaldehyde, aryl boronic acids and amino acids. The combination of synthetic, biochemical, analytical and theoretical studies allowed the identification of the 4-methoxy or the 4-diethyl amino substituent of the salicylaldehyde as the most important recognition moiety and the imine alkylation, lactone ring opening as key events in the mechanism of inhibition.

Graphical abstract: Discovery of new heterocycles with activity against human neutrophile elastase based on a boron promoted one-pot assembly reaction

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Article information


Submitted
27 Mar 2013
Accepted
10 May 2013
First published
13 May 2013

Org. Biomol. Chem., 2013,11, 4465-4472
Article type
Paper

Discovery of new heterocycles with activity against human neutrophile elastase based on a boron promoted one-pot assembly reaction

F. Montalbano, P. M. S. D. Cal, M. A. B. R. Carvalho, L. M. Gonçalves, S. D. Lucas, R. C. Guedes, L. F. Veiros, R. Moreira and P. M. P. Gois, Org. Biomol. Chem., 2013, 11, 4465
DOI: 10.1039/C3OB40614H

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