Synthesis and Preliminary Biological Evaluation of 1,3,5-Triazine Amino Acid Derivatives to Study Their MAO Inhibitors

Sherine N Khattab; Hosam H Khalil; Adnan A Bekhit; Mohamed Mokbel Abd El-Rahman; Ayman El-Faham; Fernando Albericio

doi:10.3390/molecules200915976

Synthesis and Preliminary Biological Evaluation of 1,3,5-Triazine Amino Acid Derivatives to Study Their MAO Inhibitors

Molecules. 2015 Sep 2;20(9):15976-88. doi: 10.3390/molecules200915976.

Authors

Sherine N Khattab¹, Hosam H Khalil², Adnan A Bekhit³, Mohamed Mokbel Abd El-Rahman⁴, Ayman El-Faham^{5

6}, Fernando Albericio^{7

8

9

10

11}

Affiliations

¹ Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. sh.n.khattab@gmail.com.
² Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. chemhosam1@yahoo.com.
³ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria 21521, Egypt. adnbekhit@hotmail.com.
⁴ Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. mohamedmokbel80@gmail.com.
⁵ Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. aymanel_faham@hotmail.com.
⁶ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. aymanel_faham@hotmail.com.
⁷ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. albericio@irbbarcelona.org.
⁸ Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. albericio@irbbarcelona.org.
⁹ School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa. albericio@irbbarcelona.org.
¹⁰ Institute for Research in Biomedicine and CIBER-BBN, Barcelona 08028, Spain. albericio@irbbarcelona.org.
¹¹ Department of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain. albericio@irbbarcelona.org.

Abstract

Three series of 4,6-dimethoxy-, 4,6-dipiperidino- and 4,6-dimorpholino-1,3,5-triazin-2-yl) amino acid derivatives were synthesized and characterized. A preliminary study for their monoamine oxidase inhibitory activity showed that compounds 7, 18, and 25 had MAO-A inhibition activity comparable to that of the standard clorgyline, with apparently more selective inhibitory activity toward MAO-A than MAO-B and no significant acute toxicity.

Keywords: 1,3,5-triazine derivatives; amino acids; monoamine oxidase; morpholine; piperidine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Clorgyline / pharmacology
Monoamine Oxidase Inhibitors / chemical synthesis*
Monoamine Oxidase Inhibitors / chemistry
Monoamine Oxidase Inhibitors / pharmacology
Morpholines / chemistry
Piperidines / chemistry
Quantitative Structure-Activity Relationship
Triazines / chemistry*

Substances

Amino Acids
Monoamine Oxidase Inhibitors
Morpholines
Piperidines
Triazines
piperidine
Clorgyline