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

ABSTRACT: 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.

SUBMITTER: Kallitsakis MG

PROVIDER: S-EPMC5748833 | biostudies-other | 2017

REPOSITORIES: biostudies-other

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

Kallitsakis Michael G MG Carotti Angelo A Catto Marco M Peperidou Aikaterini A Hadjipavlou-Litina Dimitra J DJ Litinas Konstantinos E KE

The open medicinal chemistry journal 20171130

<h4>Introduction</h4>The 1,3-dipolar cycloaddition reactions of nitrile oxides formed <i>in situ</i> (in the presence of NCS and Et<sub>3</sub>N) 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.<h4>Methods</h4>The new ...[more]

PMID: 29387274

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