Synthesis of New Heterocyclic Compounds Derived From  2-Amino-2-(4-Hydroxy Phenyl) Acetic Acid and Study of Their Effects on Monoamineoxidase (MAO) Activity

A. Kadhom, Sahar

	Synthesis of New Heterocyclic Compounds Derived From 2-Amino-2-(4-Hydroxy Phenyl) Acetic Acid and Study of Their Effects on Monoamineoxidase (MAO) Activity
Al-Mustansiriyah Journal of Science
Article 1, Volume 21, Issue 3, 2010, Pages 79-94
Author
Sahar A. Kadhom
Abstract
In this work 4-(4-hydroxyphenyl)- 2-methyl-oxazol-5-(4H)-one(1) was synthesized from reaction of amino acid [2-amino-2-(4-hydroxy phenyl) acetic acid] with acetic anhydride and then converted into the 1-amino-4-(4-hydroxyphenyl)-2-methyl-1H--imidazole-5(4H)-one (2) by reaction with hydrazine hydrate The azomethine (3a – d) were synthesized from the reaction of compound (2) with aromatic aldehydes. Reaction of compounds (3a – d) with 3,5-dinitrobenzoylchloride leads to addition reaction of double bond azomethine group give (4a – d) derivatives, which upon refluxing with thiourea in absolute ethanol yield 1-[(2,5-dinitrobenzoyl)[2-methyl-5-(4-hydroxyphenyl)-4-oxo-imidazol-3-(4H)-yl] amino (aryl) methyl imidothiocarbamate derivatives (5a – d). The synthesized compounds were confirmed by their IR , UV. Visible Spectra and elemental analysis (C.H.N.). Effect of the synthesized compounds on human serum MAO activity were studied, the results showed that all compounds (except compounds 4a, 4d, 5c and 5d) cause inhibition to the enzyme activity. Kinetic parameters were studied and the results showed that compounds (3a, 3c, 3d , 4b, 4c and 5a ) acted as competitive inhibitors, while compounds (1, 2, 3b and 5b ) caused mixed type of inhibition.

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