Synthesis and Biological Evaluation of Novel Hybrid Molecules Containing Purine, Coumarin and Isoxazoline or Isoxazole Moieties
Michael G. Kallitsakis1, Angelo Carotti2, Marco Catto2, Aikaterini Peperidou3, Dimitra J. Hadjipavlou-Litina3, Konstantinos E. Litinas1, *
Identifiers and Pagination:Year: 2017
First Page: 196
Last Page: 211
Publisher Id: TOMCJ-11-196
Article History:Received Date: 30/08/2017
Revision Received Date: 27/10/2017
Acceptance Date: 30/10/2017
Electronic publication date: 30/11/2017
Collection year: 2017
open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4. 0 International Public License (CC-BY 4. 0), a copy of which is available at: https://creativecommons. org/licenses/by/4. 0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ (in the presence of NCS and Et3N) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5-disubstituted isoxazolines. The similar reactions of propargyloxycoumarins or 9-propargylpurines led to 3,5-disubstituted isoxazoles by treatment with PIDA and catalytic amount of TFA.
The new compounds were tested in vitro as antioxidant agents and inhibitors of soybean lipoxygenase LO, AChE and MAO-B.
The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 4k and 4n presented LO inhibitory activity.
Compound 13e presents an antioxidant significant profile combining anti-LO, anti-AChE and anti-MAO-B activities.