(S)-1-Acetyl-2-[3-(1-pyrrolidinyl)-1-propynyl]pyrrolidine | 130523-40-9

• 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: (S)-1-Acetyl-2-[3-(1-pyrrolidinyl)-1-propynyl]pyrrolidine
• 英文别名: 1-[(2S)-2-(3-pyrrolidin-1-ylprop-1-ynyl)pyrrolidin-1-yl]ethanone
• CAS: 130523-40-9
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: JNDOCQKNQCJTBA-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (S)-1-Acetyl-2-[3-(1-pyrrolidinyl)-1-propynyl]pyrrolidine 生成 1-[(2S)-2-(3-pyrrolidin-1-ylprop-1-ynyl)pyrrolidin-1-yl]ethanone;hydrate;hydrochloride
  参考文献：
  名称：

  TRYBULSKI, EUGENE J.;KRAMSS, RICHARD H.;MANGANO, RICHARD M.;RUSINKO, ANDR+, J. MED. CHEM., 33,(1990) N2, C. 3190-3198

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S)-2-乙炔-1-吡咯烷羧酸-1,1-二甲基乙酯 在 盐酸 、 溶剂黄146 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-1-Acetyl-2-[3-(1-pyrrolidinyl)-1-propynyl]pyrrolidine
  参考文献：
  名称：

  Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogs of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5)

  摘要：

  A series of optically pure 2-[substituted-3-aminopropynyl]pyrrolidine derivatives, which are restricted-rotation analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5, compound 1), have been prepared from d- and l-proline. The compounds when tested in a series of in vitro muscarinic assays [[3H]CD (cortex), [3H]QNB (cortex), [3H]PZ (cortex), [3H]QNB (heart), [3H]QNB + GppNHp (heart)] were found to have weaker muscarinic properties than compound 1. The decrease in affinity was attributed to the increased size of the molecule resulting from the addition of a methylene group to form the pyrrolidine ring. The use of optically active compounds provided a more detailed examination of the complex pharmacological effects of the flexible muscarinic agent 1. The R enantiomers in the acetamide derivatives 12b, 12d, and 12f had a 5-10-fold greater affinity for the muscarinic receptor than the corresponding S enantiomers. A 5-fold difference or less found in the (R)- and (S)-carbamate derivatives 9, 15, and 16 suggested close overlap of the two enantiomers in the receptor binding domain. The affinity differences found in the enantiomeric acetamido derivatives when compared to those of the carbamate analogues may be the result of limited rotation of the acetamido group.

  DOI：

  10.1021/jm00174a015

文献信息

• Heterocyclic acetylenic amines having central nervous system activity
  申请人：The Upjohn Company

  公开号：US05137905A1

  公开（公告）日：1992-08-11

  Heterocyclic acetylenic amine compounds having the following structural formula ##STR1## 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.

  具有以下结构式##STR1##的杂环乙炔胺化合物具有胆碱能激动剂或拮抗剂活性，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方面有用，或作为镇痛剂用于治疗疼痛。这些化合物可用于治疗各个年龄段的认知障碍，包括老年痴呆症、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诊断出精神缺陷时改善精神表现。
• 1-Substituted-2-(3-amino-1-propynyl)-pyrrolidine derivatives
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0408879A2

  公开（公告）日：1991-01-23

  Compounds of the formula: pharmaceutical compositions containing the compounds and methods of using the compounds in the treatment of central cholinergic disfuction in a mammal are disclosed.

  式的化合物： 公开了含有这些化合物的药物组合物以及使用这些化合物治疗哺乳动物中枢胆碱能失调的方法。
• Resolved pyrrolidine, piperidine, and perhydroazepine analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
  作者：J. R. Michael Lundkvist、Hugo M. Vargas、Patrizia Caldirola、Bjoern Ringdahl、Uli Hacksell

  DOI：10.1021/jm00174a014

  日期：1990.12

  A series of conformationally restricted analogues of the partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 1) was synthesized. Three of the racemic derivatives were resolved into the enantiomers. The compounds were investigated for muscarinic and antimuscarinic activity in the isolated guinea pig ileum. They were found to be fairly potent muscarinic antagonists or weak partial agonists. The new compounds were either equally or less potent than 1 in inhibiting (-)-[3H]-N-methylscopolamine binding in homogenates of the rat cerebral cortex. Thus, structural modifications to 1 in which the amide moiety and the methyl group in the butynyl chain have been joined to form a six- or seven-membered ring preserve affinity but abolish efficacy. The R enantiomers were found to have 14-79 times higher affinity to ileal muscarinic receptors than the respective antipodes. The enantiomeric affinity ratios were nearly identical in both preparations studied. As suggested by molecular mechanics calculations, the difference in affinity between the five-membered and the six- and seven-membered ring analogues may be rationalized in conformational terms.
• TRYBULSKI, EUGENE J.;KRAMSS, RICHARD H.;MANGANO, RICHARD M.;RUSINKO, ANDR+, J. MED. CHEM., 33,(1990) N2, C. 3190-3198
  作者：TRYBULSKI, EUGENE J.、KRAMSS, RICHARD H.、MANGANO, RICHARD M.、RUSINKO, ANDR+

  DOI：——

  日期：——
• HETEROCYCLIC ACETYLENIC AMINES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0440670A1

  公开（公告）日：1991-08-14