Development of a Functionalizable External β??Turn Mimic Based on a cis??Fused 1, 7??Naphthyridine Scaffold

…, M Froeyen, SM Toppet, F Compernolle…

Index: Rombouts, Frederik J. R.; De Borggraeve, Wim M.; Delaere, David; Froeyen, Matheus; Toppet, Suzanne M.; Compernolle, Frans; Hoornaert, Georges J. European Journal of Organic Chemistry, 2003 , # 10 p. 1868 - 1878

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Citation Number: 8

Abstract

Abstract An intramolecular Diels− Alder strategy using 2 (1H)-pyrazinones was applied to generate a substituted perhydro-1, 7-naphthyridine ring system that served as a scaffold to construct the type VI β-turn mimic 2, featuring a cis-amide linkage between the central i+ 1 and i+ 2 residues. The synthesis permits mimicking of the amino acid side chains of the central dipeptide, a unique feature for external-turn mimics. Modeling studies indicated ...