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Verification of a designed intramolecular hydrogen bond in a drug scaffold by nuclear magnetic resonance spectroscopy.

Jansma, Ariane and Zhang, Qiong and Li, Bing and Ding, Qiang and Uno, Tetsuo and Bursulaya, Badry and Liu, Yi and Furet, Pascal and Gray, Nathanael and Geierstanger, Bernhard (2007) Verification of a designed intramolecular hydrogen bond in a drug scaffold by nuclear magnetic resonance spectroscopy. Journal of Medicinal Chemistry, 50 (24). pp. 5875-5877. ISSN 0022-2623

Abstract

2D 1H-15N HMBC NMR acquired at natural abundance and DMSO titration monitored by 1D 1H NMR verified the existence of an intramolecular hydrogen bond that was designed to mimic the pyrimidinone ring of a class of kinase inhibitors. A scalar coupling across the hydrogen bond was detected in organic and aqueous solvent, suggesting a simple and general approach for testing the propensity of intramolecular hydrogen bonds to stabilize pseudo-rings in drug scaffolds.

Item Type: Article
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Date Deposited: 14 Dec 2009 14:05
Last Modified: 31 Jan 2013 01:28
URI: https://oak.novartis.com/id/eprint/104

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