N-(4-Diethylamino-2-butynyl)-2-pyrrolidone | 6205-21-6

• 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-(4-Diethylamino-2-butynyl)-2-pyrrolidone
• 英文别名: N-<4-(diethylamino)-2-butynyl>-2-pyrrolidone；1-(4-Diethylamino-but-2-inyl)-pyrrolidin-2-on；1-[4-(diethylamino)-2-butynyl]-2-pyrrolidinone；1-[4-(Diethylamino)but-2-YN-1-YL]pyrrolidin-2-one；1-[4-(diethylamino)but-2-ynyl]pyrrolidin-2-one
• CAS: 6205-21-6
• 化学式: C₁₂H₂₀N₂O
• 分子量: 208.304
• InChiKey: PSKNGGAYTKVTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-Diethylamino-2-butynyl)-2-pyrrolidone 在 溴化氰 、 silver perchlorate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 <4-(2-oxopyrrolidinyl)-2-butynyl>dimethylsulfonium perchlorate
  参考文献：
  名称：

  Dimethylsulfonium and thiolanium analogs of the muscarinic agent oxotremorine

  摘要：

  Dimethylsulfonium (6a and 6b) and thiolanium analogues (7a and 7b) of oxotremorine were synthesized and found to be potent muscarinic agents in vivo and vitro. Compound 6a exceeded oxotremorine in potency. Their affinities for muscarinic receptors in the guinea pig ileum and urinary bladder, estimated pharmacologically, were higher than those of the corresponding trimethylammonium (8a and 8b) and N-methylpyrrolidinium compounds (9a and 9b). However, the new compounds had lower intrinsic efficacies than their quaternary ammonium analogues. The compounds also had high affinity for central muscarinic receptors as measured by displacement of specifically bound (-)-[3H]-N-methylscopolamine from homogenates of the rat cerebral cortex. Half-maximal occupation of cortical muscarinic receptors by 6a, 6b, 7a, and 7b was achieved at concentrations of 0.8, 5.4, 0.3, and 3.3 microM, respectively. The competition curves of 6a, 6b, and 7a were adequately described by a two-site binding equation. The ratio of low- and high-affinity dissociation constants agreed with relative efficacy estimated on the ileum. The thiolanium salt 7a was a fairly potent nicotinic agent on the frog rectus abdominis.

  DOI：

  10.1021/jm00396a025
• 作为产物：
  描述：

  聚合甲醛 、 1-丙炔-2-吡咯烷-2-酮 、 二乙胺 在 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-(4-Diethylamino-2-butynyl)-2-pyrrolidone
  参考文献：
  名称：

  炔属咪唑和相关化合物的胆碱能活性。

  摘要：

  制备了一系列与oxotremorine相关的炔属咪唑（1a），并通过体外结合试验和小鼠体内药理学试验评估了它们为胆碱能药物。1- [4-（1H-咪唑-1-基）-2-丁炔基] -2-吡咯烷酮（1b）是胆碱能激动剂，氧代雷莫林的效力为二分之一。在咪唑环中具有5-或2-甲基取代基的1b的类似物（化合物1c和1g）是胆碱能部分激动剂。1b在吡咯烷酮环的5位（7b）或炔链的α位（8b）具有甲基取代基的类似物是拮抗剂。制备了这些咪唑乙炔的各种类似物，其中吡咯烷酮环被酰胺，氨基甲酸酯或尿素残基取代。含有5-甲基咪唑作为胺取代基的几种化合物是部分激动剂。将咪唑化合物的活性与相关的吡咯烷和二甲胺类似物的活性进行比较。提出了这些化合物在毒蕈碱受体上的激动剂和拮抗剂构象。

  DOI：

  10.1021/jm00112a002

文献信息

• Acetylenic imidazoles having central nervous system activity
  申请人：The Upjohn Company

  公开号：US05100909A1

  公开（公告）日：1992-03-31

  Acetylenic imidazole compounds having cholinergic agonist or antagonist activity useful in the treatment of mental disorders, extrapyramidal motor disorders, disorders of the parasympathetic nervous system and glaucoma or as analgesics for the treatment of pain. Typical central nervous system disorders for which the subject compounds can be used include cognitive disorders of all ages, including senile dementia, Alzheimer's disease and other related disorders. The compounds are particularly developed to improve mental performance when a mental deficiency is diagnosed.

  含有胆碱能激动剂或拮抗剂活性的乙炔基咪唑化合物在治疗精神障碍、锥体外运动障碍、副交感神经系统障碍和青光眼，或作为镇痛剂治疗疼痛方面具有用处。这些化合物可用于治疗典型的中枢神经系统障碍，包括各个年龄段的认知障碍，如老年性痴呆症、阿尔茨海默病和其他相关疾病。这些化合物特别被开发用于在确诊为智力缺陷时改善精神表现。
• Synthesis and pharmacological properties of <i>N</i>-[4-(1-azetidinyl)-2- butynyl]-2-pyrrolidone, a highly potent oxotremorine-like agent
  作者：B Resul、T Lewander、T Zetterström、B Ringdahl、Z Muhi-Eldeen、R Dahlbom

  DOI：10.1111/j.2042-7158.1980.tb12964.x

  日期：2011.4.12
• ACETYLENIC IMIDAZOLES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0426714B1

  公开（公告）日：1996-04-03
• US4065471A
  申请人：——

  公开号：US4065471A

  公开（公告）日：1977-12-27
• US5100909A
  申请人：——

  公开号：US5100909A

  公开（公告）日：1992-03-31