Verification of a Designed Intramolecular Hydrogen Bond in a Drug Scaffold by Nuclear Magnetic Resonance Spectroscopy

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• 作者：Ariane Jansma ; Qiong Zhang ; Bing Li ; Qiang Ding ; Tetsuo Uno ; Badry Bursulaya ; Yi Liu ; Pascal Furet ; Nathanael S. Gray ; Bernhard H. Geierstanger
• 刊名：Journal of Medicinal Chemistry
• 出版年：2007
• 出版时间：November 29, 2007
• 年：2007
• 卷：50
• 期：24
• 页码：5875 - 5877
• 全文大小：82K
• 年卷期：v.50,no.24(November 29, 2007)
• ISSN：1520-4804

文摘

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