Regio- and stereoselective cycloadditions of cyclic nitrones to maleic diamide forced in a peptide: synthesis of potent ligands of human NK-2 receptor.
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.
Valenza
S
S
Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy.
Cordero
F M
FM
Brandi
A
A
Guidi
A
A
Altamura
M
M
Giolitti
A
A
Giuntini
F
F
Pasqui
F
F
Renzetti
A R
AR
Maggi
C A
CA
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*
D004151:Dipeptides; D007202:Indicators and Reagents; D008024:Ligands; D009589:Nitrogen Oxides; D018041:Receptors, Neurokinin-2; D015320:Tachykinins; C015388:nitrones