title: Regio- and stereoselective cycloadditions of cyclic nitrones to maleic diamide forced in a peptide: synthesis of potent ligands of human NK-2 receptor.
abstract: The regioselectivity and the stereoselectivity induced by relatively small peptidomimetic maleic diamide 1 in cycloaddition reactions with cyclic nitrones 2-5 was studied. The high regio- and stereoselectivity observed, sensibly increased by nonpolar solvents, was the effect of a double-asymmetric induction produced by the nitrone substituent on the pseudopeptidic tether. A new class of potent human tachykinin NK-2 receptor ligands was synthesized.
authors.affiliation: Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Valenza
authors.forename: F M
authors.initials: FM
authors.lastname: Cordero
authors.forename: A
authors.initials: A
authors.lastname: Brandi
authors.forename: A
authors.initials: A
authors.lastname: Guidi
authors.forename: M
authors.initials: M
authors.lastname: Altamura
authors.forename: A
authors.initials: A
authors.lastname: Giolitti
authors.forename: F
authors.initials: F
authors.lastname: Giuntini
authors.forename: F
authors.initials: F
authors.lastname: Pasqui
authors.forename: A R
authors.initials: AR
authors.lastname: Renzetti
authors.forename: C A
authors.initials: CA
authors.lastname: Maggi
mesh_terms: D004151:Dipeptides / Q000737:chemistry* / Q000493:pharmacokinetics; D006801:Humans; D007202:Indicators and Reagents; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D018041:Receptors, Neurokinin-2 / Q000378:metabolism*; D013329:Structure-Activity Relationship; D015320:Tachykinins / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D007202:Indicators and Reagents; D008024:Ligands; D009589:Nitrogen Oxides; D018041:Receptors, Neurokinin-2; D015320:Tachykinins; C015388:nitrones