γ-N,N-dimethylamiopropyl 2,2-diphenylpropionate | 3579-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: γ-N,N-dimethylamiopropyl 2,2-diphenylpropionate
• 英文别名: 2,2-diphenyl-propionic acid-(3-dimethylamino-propyl ester)；2,2-Diphenyl-propionsaeure-(3-dimethylamino-propylester)；3-(Dimethylamino)propyl 2,2-diphenylpropanoate
• CAS: 3579-27-9
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: HWNNSDYCTCTMOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-二苯基丙酸 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 γ-N,N-dimethylamiopropyl 2,2-diphenylpropionate
  参考文献：
  名称：

  Relationship of the crystal structure of ?-N,N-dimethylaminopropyl 2,2-diphenylpropionate hydrochloride to antimuscarinic activity

  摘要：

  The title compound was synthesized, characterized by H-1 nmr, and crystallized for x-ray crystallography. The antimuscarinic potency of the title compound was about equipotent to aprophen or atropine in inhibiting acetylcholine-induced contraction of guinea pig ileum (K(B) = 4.5 nM) and in inhibiting carbachol-stimulated release of alpha-amylase from rat pancreatic acinar cells (K(i) = 1.4 nM), and in inhibiting the binding of [N-methyl-H-3]scopolamine to cerebral cortex (K(i) = 6.6 nM). In the crystal, the O-C-C-C-N+ segment adopted a gauche-gauche configuration resulting in an N+ ... O (carbonyl) distance of 5.001(9) angstrom, a distance comparable to that in aprophen. The ether oxygen atom is buried rendering it inaccessible for interaction with the muscarinic receptor. The carbonyl oxygen atom is exposed to the surface of the molecule and is readily accessible for intermolecular interactions. The similarity in biological activities of the title compound and aprophen is congruous with their similar N+ ... O (carbonyl) distances.

  DOI：

  10.1007/bf01195411

文献信息

• Relationship of the crystal structure of ?-N,N-dimethylaminopropyl 2,2-diphenylpropionate hydrochloride to antimuscarinic activity
  作者：Jean M. Karle、Isabella L. Karle、Haim Leader、Eli Breuer、Amy H. Newman、Richard K. Gordon、Peter K. Chiang

  DOI：10.1007/bf01195411

  日期：1992.8

  The title compound was synthesized, characterized by H-1 nmr, and crystallized for x-ray crystallography. The antimuscarinic potency of the title compound was about equipotent to aprophen or atropine in inhibiting acetylcholine-induced contraction of guinea pig ileum (K(B) = 4.5 nM) and in inhibiting carbachol-stimulated release of alpha-amylase from rat pancreatic acinar cells (K(i) = 1.4 nM), and in inhibiting the binding of [N-methyl-H-3]scopolamine to cerebral cortex (K(i) = 6.6 nM). In the crystal, the O-C-C-C-N+ segment adopted a gauche-gauche configuration resulting in an N+ ... O (carbonyl) distance of 5.001(9) angstrom, a distance comparable to that in aprophen. The ether oxygen atom is buried rendering it inaccessible for interaction with the muscarinic receptor. The carbonyl oxygen atom is exposed to the surface of the molecule and is readily accessible for intermolecular interactions. The similarity in biological activities of the title compound and aprophen is congruous with their similar N+ ... O (carbonyl) distances.