2001 pyridine derivatives

pyridine derivativesR 0380

12 - 143Enantiopure 4- and 5-Aminopiperidin-2-ones: Regiocontrolled Syn-thesis and Conformational Characterization as Bioactive β-TurnMimetics. — The aminopiperidinones (VII) and (XVIII) undergo di-astereoselective alkylation after N-protection yielding trans- or cis-substitutedderivatives like (XI) and (XX). The peptidomimetic (XXII) generated from(VII) is found to adopt predominantly a reverse-turn structure, whereas theisomer (XXIII) adopts a half-chair conformation. Additionally, it is foundthat the peptidomimetic (XXIV) significantly enhances the agonist binding ofdopamine D2 receptors and reveals an activity comparable to Pro-Leu-Gly-NH2.— (WEBER, KLAUS; OHNMACHT, URSULA; GMEINER, PETER; J. Org.Chem. 65 (2000) 22, 7406-7416; Dep. Med. Chem., Emil Fischer Cent.,Friedrich-Alexander Univ., D-91052 Erlangen, Germany; EN)

1

2001 pyridine derivatives

2