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Title: Development of a functionalizable external beta-turn mimic based on a cis-fused 1,7-naphthyridine scaffold
Authors: Rombouts, FJR ×
De Borggraeve, Wim
Delaere, David
Froeyen, Mathy
Toppet, SM
Compernolle, Frans
Hoornaert, GJ #
Issue Date: Jan-2003
Publisher: Wiley-v c h verlag gmbh
Series Title: European journal of organic chemistry issue:10 pages:1868-1878
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 beta-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 that the cis-fused bicyclic system adopts a conformation suitable for induction of a beta-turn when the angular position 8a bears a non-H substituent. Extensive NMR analysis of an 8a-methyl derivative 25 confirmed its beta-turn-inducing properties in various solvents, including water. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
ISSN: 1434-193X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Molecular Design and Synthesis
× corresponding author
# (joint) last author

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