Synthesis and dopamine receptor modulating activity of 3-substituted γ-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide

Kristine Dolbeare, Giuseppe F. Pontoriero, Suresh K. Gupta, Ram K. Mishra, Rodney L. Johnson

Research output: Contribution to journalArticle

43 Scopus citations

Abstract

γ-Lactam peptidomimetic 2 of Pro-Leu-Gly-NH2 (PLG) was substituted at the 3-position with isobutyl, butyl, and benzyl moieties to give the PLG peptidomimetics 3-5, respectively. These compounds were synthesized to test the hypothesis that attaching a hydrophobic moiety to the lactam ring to mimic the isobutyl side chain of the leucyl residue of PLG would increase the dopamine receptor modulating activity of such peptidomimetics. These peptidomimetics were tested for their ability to enhance the binding of [3H]-N-propylnorapomorphine to dopamine receptors isolated from bovine striatal membranes. The rank order of effectiveness of the 3-substituent was benzyl > n-butyl > isobutyl > H.

Original languageEnglish (US)
Pages (from-to)727-733
Number of pages7
JournalJournal of Medicinal Chemistry
Volume46
Issue number5
DOIs
StatePublished - Feb 27 2003

Fingerprint Dive into the research topics of 'Synthesis and dopamine receptor modulating activity of 3-substituted γ-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide'. Together they form a unique fingerprint.

  • Cite this