Regio- and stereoselective cycloadditions of cyclic nitrones to maleic diamide forced in a peptide: Synthesis of potent ligands of human NK-2 receptor

Authors
Valenza, S Cordero, FM Brandi, A Guidi, A Altamura, M Giolitti, A Giuntini, F Pasqui, F Renzetti, AR Maggi, CA
Citation
S. Valenza et al., Regio- and stereoselective cycloadditions of cyclic nitrones to maleic diamide forced in a peptide: Synthesis of potent ligands of human NK-2 receptor, J ORG CHEM, 65(13), 2000, pp. 4003-4008
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
13
Year of publication
2000
Pages
4003 - 4008
Database
ISI
SICI code
0022-3263(20000630)65:13<4003:RASCOC>2.0.ZU;2-U
Abstract
The regioselectivity and the stereoselectivity induced by relatively small peptidomimetic maleic diamide 1 in cycloaddition reactions with cyclic nitr ones 2-5 was studied. The high regio- and stereoselectivity observed, sensi bly increased by nonpolar solvents, was the effect of a double-asymmetric i nduction produced by the nitrone substituent on the pseudopeptidic tether. A new class of potent human tachykinin NK-2 receptor ligands was synthesize d.