Lessene Guillaume, Smith Brian J, Gable Robert W, Baell Jonathan B
The Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Victoria 3052, Australia.
J Org Chem. 2009 Sep 4;74(17):6511-25. doi: 10.1021/jo900871a.
The ability of the benzoylurea core to mimic alpha helices relies on its ability to form an intramolecular hydrogen bond. The conformational behavior of benzoylureas is investigated in depth in this study via the use of NMR, IR, X-ray, and computational analysis. The results show that the closed conformation maintained by an intramolecular hydrogen bond is favored in most of the cases studied except when steric and electronic effects combined with a solvent possessing a high hydrogen bond accepting ability, such as DMSO, are involved. The study highlights the propensity for benzoylureas to switch conformation depending on the environment of the molecule for a particular set of substituents. We anticipate that our summary of the phenomenon of internal hydrogen bonding and its analysis may further serve as a useful reference source for future workers in this area.
苯甲酰脲核心模拟α螺旋的能力依赖于其形成分子内氢键的能力。本研究通过核磁共振（NMR）、红外光谱（IR）、X射线和计算分析等方法，对苯甲酰脲的构象行为进行了深入研究。结果表明，在大多数研究案例中，由分子内氢键维持的封闭构象是有利的，除非涉及空间和电子效应以及具有高氢键接受能力的溶剂（如二甲基亚砜，DMSO）。该研究突出了苯甲酰脲根据特定取代基分子环境改变构象的倾向。我们预计，我们对分子内氢键现象的总结及其分析可能会为该领域的未来研究人员提供有用的参考来源。
