N-propargyl-4-phenyl-2-pyrrolidone | 137518-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-propargyl-4-phenyl-2-pyrrolidone
• 英文别名: 4-Phenyl-1-prop-2-ynylpyrrolidin-2-one
• CAS: 137518-26-4
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: CDJPSUGJIFJSDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 聚合甲醛 、 N-propargyl-4-phenyl-2-pyrrolidone 在 溶剂黄146 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以97%的产率得到4-Phenyl-1-(4-pyrrolidin-1-ylbut-2-ynyl)pyrrolidin-2-one
  参考文献：
  名称：

  Phenyl-substituted analogs of oxotremorine as muscarinic antagonists

  摘要：

  A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared. The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice. They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)-[H-3]-N-methylscopolamine to homogenates of the rat cerebral cortex. The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity. Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues. The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (K(D)) of 0.10 and 0.20-mu-M, respectively, in the ileum assay. The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted positional isomers. A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.

  DOI：

  10.1021/jm00080a013
• 作为产物：
  描述：

  4-硝基-3-苯基丁酸乙酯 在 palladium on activated charcoal 氢氧化钾 、 四丁基溴化铵 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-propargyl-4-phenyl-2-pyrrolidone
  参考文献：
  名称：

  Phenyl-substituted analogs of oxotremorine as muscarinic antagonists

  摘要：

  A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared. The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice. They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)-[H-3]-N-methylscopolamine to homogenates of the rat cerebral cortex. The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity. Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues. The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (K(D)) of 0.10 and 0.20-mu-M, respectively, in the ileum assay. The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted positional isomers. A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.

  DOI：

  10.1021/jm00080a013

文献信息

• [EN] ALKYNYL AMINES THAT REGULATE CHOLINERGIC NEUROTRANSMISSION
  申请人：ABBOTT LABORATORIES

  公开号：WO1991000724A1

  公开（公告）日：1991-01-24

  (EN) A compound that regulates cortical cholinergic neurotransmission of formula (I), wherein A is (1) a functionalized lactam; (2) a a functionalized azacycloalkyl group; (3) a functionalized carbonylaminomethyl group; or (4) a functionalized oxyalkyl group; and B is (1) a functionalized pyrrolidin-2-yl group; (2) a functionalized aminomethyl group; (3) a 5-membered heterocycle containing two heteroatoms; or (4) a piperidine derivative; or a pharmaceutically acceptable salt thereof.(FR) L'invention concerne un composé de régulation de la neurotransmission cholinergique corticale ayant la formule (I), dans laquelle A représente (1) une lactame fonctionnalisée; (2) un groupe azacycloalkyle fonctionnalisé; (3) un groupe carbonylaminométhyle fonctionnalisé; ou (4) un groupe oxyalkyle fonctionnalisé; et B représente (1) un groupe pyrrolidine-2-yl fonctionnalisé; (2) un groupe aminométhyle fonctionnalisé; (3) un hétérocycle à 5 membres contenant deux hétéro-atomes; ou (4) un dérivé de pipéridine, ou son sel pharmaceutiquement acceptable.