(-)-(R)-4-amino-1-cyclopent-1-enyl(methyl)phosphinic acid | 867063-38-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (-)-(R)-4-amino-1-cyclopent-1-enyl(methyl)phosphinic acid
• 英文别名: (R)-4-ACPMPA；(R)-(4-aminocyclopent-1-enyl)methylphosphinic acid；[(4R)-4-aminocyclopenten-1-yl]-methylphosphinic acid
• CAS: 867063-38-5
• 化学式: C₆H₁₂NO₂P
• 分子量: 161.141
• InChiKey: COSQDVKDGWGBPW-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R)-4-amino-1-cyclopent-1-enyl(methyl)phosphinic acid 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 N,O-双(三甲基硅烷基)三氟乙酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 58.0h， 生成 methyl((R)-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)cyclopent-1-enyl)phosphinic acid
  参考文献：
  名称：

  Novel γ-Aminobutyric Acid ρ₁Receptor Antagonists; Synthesis, Pharmacological Activity and Structure−Activity Relationships

  摘要：

  gamma-Aminobutyric acid (GABA) analogues based on 4-amino-cyclopent-1-enyl phosphinic acid (34-42) and 3-aminocyclobutane phosphinic acids (51, 52, 56, 57) were investigated in order to obtain selective homomeric rho(1) GABA(C) receptor antagonists. The effect of the stereochemistry and phosphinic acid substituent of these compounds on potency and selectivity within the GABA receptor subtypes was investigated. Compounds of high potency at GABA(C) rho(1) receptors (36, K-B = 0.78 mu M) and selectivity greater than 100 times (41, K-B = 4.97 mu M) were obtained. The data obtained was analyzed along with the known set of GABA(C) rho(1) receptor-ligands, leading to the development of a pharmacophore model for this receptor, which can be used for in silico screening.

  DOI：

  10.1021/jm7015842
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 反应 30.0h， 生成 (-)-(R)-4-amino-1-cyclopent-1-enyl(methyl)phosphinic acid
  参考文献：
  名称：

  Novel γ-Aminobutyric Acid ρ₁Receptor Antagonists; Synthesis, Pharmacological Activity and Structure−Activity Relationships

  摘要：

  gamma-Aminobutyric acid (GABA) analogues based on 4-amino-cyclopent-1-enyl phosphinic acid (34-42) and 3-aminocyclobutane phosphinic acids (51, 52, 56, 57) were investigated in order to obtain selective homomeric rho(1) GABA(C) receptor antagonists. The effect of the stereochemistry and phosphinic acid substituent of these compounds on potency and selectivity within the GABA receptor subtypes was investigated. Compounds of high potency at GABA(C) rho(1) receptors (36, K-B = 0.78 mu M) and selectivity greater than 100 times (41, K-B = 4.97 mu M) were obtained. The data obtained was analyzed along with the known set of GABA(C) rho(1) receptor-ligands, leading to the development of a pharmacophore model for this receptor, which can be used for in silico screening.

  DOI：

  10.1021/jm7015842

文献信息

• Neurologically-Active Compounds
  申请人：Chebib Mary

  公开号：US20080032950A1

  公开（公告）日：2008-02-07

  The invention provides a compound of the formula I: wherein R is methyl, ethyl, propyl, isopropyl, butyl, pentyl, neo-pentyl or cyclohexyl, or a salt or solvate thereof. These compounds are selective GABA C receptor antagonists. The invention also provides pharmaceutical compositions comprising a compound of formula I or a pharmaceutically acceptable salt or solvate thereof. The invention also provides methods of enhancing the cognitive activity of an animal and methods of stimulating memory capacity in an animal, comprising the step of administering to the animal an effective amount of a compound of formula I or a pharmaceutically acceptable salt or solvate thereof.

  本发明提供一种化合物，其化学式为I：其中R为甲基、乙基、丙基、异丙基、丁基、戊基、新戊基或环己基，或其盐或溶剂化物。这些化合物是选择性的GABAC受体拮抗剂。本发明还提供包括化合物I或其药学上可接受的盐或溶剂化物的制药组合物。本发明还提供增强动物认知活动和刺激动物记忆能力的方法，其中包括向动物施用化合物I或其药学上可接受的盐或溶剂化物的有效量。
• NEUROLOGICALLY-ACTIVE COMPOUNDS
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：EP1773740B1

  公开（公告）日：2009-02-18