Synthesis and Biological Evaluation of Novel Hybrid Molecules Containing Purine, Coumarin and Isoxazoline or Isoxazole Moieties

Kallitsakis, Michael G.; Carotti, Angelo; Catto, Marco; Peperidou, Aikaterini; Hadjipavlou-Litina, Dimitra J.; Litinas, Konstantinos E.

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. Litinas^{1, *}

¹ Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

² Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari “Aldo Moro”, V. Orabona 4, I-70125 Bari, Italy

³ Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

Article Information

Identifiers and Pagination:

Year: 2017
Volume: 11
First Page: 196
Last Page: 211
Publisher ID: TOMCJ-11-196
DOI: 10.2174/1874104501711010196

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

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© 2017 Kallitsakis et al.

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.

^* Address correspondence to this authors at the Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece; Tel: +302310997864; Fax: +302310997679; E-mail: klitinas@chem.auth.gr

Introduction:

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.

Methods:

The new compounds were tested in vitro as antioxidant agents and inhibitors of soybean lipoxygenase LO, AChE and MAO-B.

Results:

The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 4k and 4n presented LO inhibitory activity.

Conclusion:

Compound 13e presents an antioxidant significant profile combining anti-LO, anti-AChE and anti-MAO-B activities.

Keywords: Modified Homo-N-nucleosides, Purines, Coumarins, 1,3-dipolar Cycloaddition Reaction, Antioxidant activity, Anti-lipid peroxidation activity, Alzheimer’s Disease.

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RESEARCH ARTICLE

Synthesis and Biological Evaluation of Novel Hybrid Molecules Containing Purine, Coumarin and Isoxazoline or Isoxazole Moieties

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