(R)-2-<3-(1-pyrrolidinyl)-1-propynyl>-1-(trifluoroacetyl)pyrrolidine | 130523-47-6

• 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: (R)-2-<3-(1-pyrrolidinyl)-1-propynyl>-1-(trifluoroacetyl)pyrrolidine
• 英文别名: (R)-2-[3-(1-pyrrolidinyl)-1-propynyl]-1-(trifluoroacetyl)pyrrolidine；(2R)-2-[3-(Pyrrolidin-1-yl)-1-propynyl]-1-(trifluoroacetyl)pyrrolidine；2,2,2-trifluoro-1-[(2R)-2-(3-pyrrolidin-1-ylprop-1-ynyl)pyrrolidin-1-yl]ethanone
• CAS: 130523-47-6
• 化学式: C₁₃H₁₇F₃N₂O
• 分子量: 274.286
• InChiKey: ICQDNYCEUCZFNR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 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：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-<3-(1-pyrrolidinyl)-1-propynyl>-1-(trifluoroacetyl)pyrrolidine 生成 2,2,2-trifluoro-1-[(2R)-2-(3-pyrrolidin-1-ylprop-1-ynyl)pyrrolidin-1-yl]ethanone;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：

  (R)-2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-2-<3-(1-pyrrolidinyl)-1-propynyl>-1-(trifluoroacetyl)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

• 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。
• 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：——
• US5001142A
  申请人：——

  公开号：US5001142A

  公开（公告）日：1991-03-19
• US5128483A
  申请人：——

  公开号：US5128483A

  公开（公告）日：1992-07-07
• Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogs of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5)
  作者：Eugene J. Trybulski、Richard H. Kramss、Richard M. Mangano、Andrew Rusinko

  DOI：10.1021/jm00174a015

  日期：1990.12

  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.