N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]acetamide | 130403-61-1

• 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-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]acetamide
• 英文别名: Acetamide, N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]-；N-[4-(3-hydroxypyrrolidin-1-yl)but-2-ynyl]-N-methylacetamide
• CAS: 130403-61-1
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: JNJULLPRDPZIGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]acetamide 生成 N-[4-(3-fluoropyrrolidin-1-yl)but-2-ynyl]-N-methylacetamide;oxalic acid
  参考文献：
  名称：

  BRADBURY, BARTON J.;BAUMGOLD, JESSE;PAEK, ROBERT;KAMMULA, UDAI;ZIMMET, JE+, J. MED. CHEM., 34,(1991) N, C. 1073-1079

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基吡咯烷 、 N-甲基-N-(2-丙炔)乙酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 copper(l) chloride 作用下， 生成 N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]acetamide
  参考文献：
  名称：

  Muscarinic receptor binding and activation of second messengers by substituted N-methyl-N-[4-(1-azacycloalkyl)-2-butynyl]acetamides

  摘要：

  A series of substituted azacycloalkyl analogues of the muscarinic agonist UH 5 (N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]acetamide, 1a) were synthesized and evaluated pharmacologically. These compounds were developed as intermediates for further derivatization leading to functionalized congeners of 1a. The compounds were synthesized by using a Mannich-type condensation of N-acetyl-N-methylpropargylamine to various substituted saturated azaheterocycles. The compounds were screened at a single concentration in competitive binding assays in rat cerebral cortical membranes against either [H-3]N-methylscopolamine (at 100-mu-M) or [H-3]oxotremorine-M (at 1-mu-M) labels. Candidates were then selected for further evaluation of their effect on phosphoinositide (PI) turnover in membranes from A9L cells transfected with cDNA of either m1-muscarinic cholinergic receptors (m1AChRs) or m3AChRs. The analogues were also tested for the inhibition of adenylate cyclase in NG108-15 cells expressing m4AChRs. The azetidine analogue of 1a had a K(i) value of 12 nM for the inhibition of [H-3]oxotremorine-M binding in rat brain and had an agonist potency at m1-, m3-, and m4AChRs comparable to 1a. The substituted 5- and 6-member ring analogues generally had lower binding affinities and were less potent than 1a in stimulating PI turnover. Several compounds were moderately effective in inhibiting cyclic AMP production in NG108-15 cells.

  DOI：

  10.1021/jm00107a029

文献信息

• 3- or 4-substituted oxotremorine derivatives
  申请人：American Cyanamid Company

  公开号：US04937235A1

  公开（公告）日：1990-06-26

  This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.

  本公开说明了具有极性取代氧或硫基团的新型3或4取代氧托莫林衍生物。这些化合物具有胆碱能活性。还公开了使用这些化合物治疗哺乳动物中枢神经系统疾病的方法，含有这些化合物的制药制剂以及生产这些化合物的过程。
• 3- or 4-substituted oxotremorine derivatives and a method of treating
  申请人：American Cyanamid Company

  公开号：US04952600A1

  公开（公告）日：1990-08-28

  This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.

  本文披露了一种新型的3或4取代氧化戊烯衍生物，其具有带极性取代的氧或硫基团。这些化合物具有胆碱能活性。还披露了使用这些化合物治疗哺乳动物中枢神经系统疾病的方法，含有这些化合物的药物制剂以及这些化合物的生产过程。
• US4937235A
  申请人：——

  公开号：US4937235A

  公开（公告）日：1990-06-26
• US4952600A
  申请人：——

  公开号：US4952600A

  公开（公告）日：1990-08-28
• US5089518A
  申请人：——

  公开号：US5089518A

  公开（公告）日：1992-02-18