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Bioorg Med Chem Lett. 2013 Apr 1;23(7):1949-52. doi: 10.1016/j.bmcl.2013.02.046. Epub 2013 Feb 16.

Synthesis, receptor binding and activity of iso and azakainoids.

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  • 1Department of Chemistry and Biochemistry, Florida International University, 11200 SW 8th Str., Miami, FL 33199, USA.

Abstract

Two syntheses for the production of an unsubstituted azakainoid are described. The 1,3-dipolar cycloaddition of diazomethane with trans-dibenzyl glutaconate yields a 1-pyrazoline, which may be reduced directly to the pyrazolidine. An unexpected trans-cis isomerization is observed during Hg/Al reduction of the 1-pyrazoline NN bond. Alternatively, when TMS diazomethane is used as the dipole, the resulting 2-pyrazoline obtained after desilylation may be reduced with NaCNBH3 to provide the trans azakainate analog exclusively. The synthesis of an unsubstituted isokainoid via Michael addition is also described. Glutamate receptor binding assays revealed that the azakaniod has a moderate affinity for unspecified glutamate receptors. Membrane depolarization of Aplysia neurons upon application of the azakainoid demonstrates that it is an ionotropic glutamate receptor agonist.

Copyright © 2013 Elsevier Ltd. All rights reserved.

PMID:
23481645
[PubMed - indexed for MEDLINE]
PMCID:
PMC3601572
Free PMC Article

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