首页> 外文期刊>Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry >STRUCTURAL AND CONFORMATIONAL STUDIES ON 5-[l '-METHYLPYRROLIDIN-2'-YL]-l,3-OXAZOLIDIN-2-ONE FREE BASE AND HYDROCHLORIDE FORM
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STRUCTURAL AND CONFORMATIONAL STUDIES ON 5-[l '-METHYLPYRROLIDIN-2'-YL]-l,3-OXAZOLIDIN-2-ONE FREE BASE AND HYDROCHLORIDE FORM

机译:5- [l'-甲基吡咯烷基-2'-YL] -1,3-恶唑啉-2-酮游离碱和盐酸盐形式的结构和构型研究

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摘要

The molecular structures of (5R,2'S)-5-[1'-methylpyrrolidin-2'-yl]-l,3-oxazolidin-2-one free base (1) and its enantiomeric hydrochloride salt (2) have been determined in order to understand their interaction at neuronal acetylcholine receptor. The molecules are in a bent conformation with the pyrrolidine and the oxazolidinone rings nearly at 60 deg to each other. The molecular assembly is characterized by the formation of chains joined via hydrogen bonds N-H...N in 1 and N-H...C1 in 2. The solid state structures have been compared with the theoretical conformations and docked into the crystal structure of Acetylcholine Binding Protein (AChBP), homolog of the ligand binding domain of nAChR. A closer analogy between the receptor bound conformation and the solid state has been found in the hydrochoride form with respect to the free base. This latter (1) forms an hydrogen bond with Trp 6702, while 2 beside two additional interactions with Trp 6702 is linked also to Ile 118.
机译:(5R,2'S)-5- [1'-甲基吡咯烷-2'-基] -1,3-恶唑烷-2-一游离碱(1)及其对映体盐酸盐(2)的分子结构已在为了了解它们在神经元乙酰胆碱受体上的相互作用。这些分子与吡咯烷和恶唑烷酮环成彼此几乎成60度的弯曲构型。分子组装的特征是通过氢键1中的NH ... N和2中的NH ... C1连接的链形成。已将固态结构与理论构型进行了比较,并进入了乙酰胆碱键合的晶体结构蛋白质(AChBP),nAChR的配体结合域的同源物。相对于游离碱,已经发现以氢氯化物形式的受体结合的构象与固态之间的更接近的类比。后者(1)与Trp 6702形成氢键,而与Trp 6702的另外两个相互作用之外的2也与Ile 118连接。

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