(+/-)-2-(4-phenylbutyryl)cyclopent-2-enecarboxylic acid | 725265-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (+/-)-2-(4-phenylbutyryl)cyclopent-2-enecarboxylic acid
• 英文别名: 2-(4-phenylbutanoyl)-cyclopent-2-ene-carboxylic acid；2-(4-Phenylbutanoyl)cyclopent-2-ene-1-carboxylic acid
• CAS: 725265-82-7
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: BUFVLAUIGPPSTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(4-phenylbutyryl)cyclopent-2-enecarboxylic acid 在 lithium hydroxide 、 氯甲酸乙酯 、 三甲基乙酰氯 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.83h， 生成 1-[2-(4-phenylbutyryl)cyclopent-2-enecarbonyl]pyrrolidine-2(S)-nitrile
  参考文献：
  名称：

  A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors

  摘要：

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.

  DOI：

  10.1021/jm049503w
• 作为产物：
  描述：

  (+/-)-2-formylcyclopent-2-enecarboxylic acid 在 草酰氯 、 碘 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (+/-)-2-(4-phenylbutyryl)cyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors

  摘要：

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.

  DOI：

  10.1021/jm049503w

文献信息

• Compounds having prolyl oligopeptidase inhibitory activity
  申请人：Gynther Jukka

  公开号：US20060229254A1

  公开（公告）日：2006-10-12

  A compound of formula (I), wherein X, R 1 , R 2 and R 3 are as defined in the disclosure, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia.

  式(I)的化合物，其中X、R1、R2和R3如所披露的定义，或其药学上可接受的盐或酯，可用作脯氨酰寡肽酶抑制剂。这些化合物可用于治疗需要脯氨酰寡肽酶抑制剂具有疗效的疾病或情况，例如用于治疗神经退行性疾病，如阿尔茨海默病和老年性痴呆症。
• COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY
  申请人：Orion Corporation

  公开号：EP1581489A2

  公开（公告）日：2005-10-05
• [EN] COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY<br/>[FR] COMPOSES PRESENTANT UN EFFET INHIBITEUR SUR LA PROLYL-OLIGOPEPTIDASE
  申请人：ORION CORP

  公开号：WO2004060862A2

  公开（公告）日：2004-07-22

  The invention provides a compound of formula (I), wherein in the formula X, R1, R2 and R3 are as defined in claim 1, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds of formula (I) can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia
• A Cyclopent-2-enecarbonyl Group Mimics Proline at the P2 Position of Prolyl Oligopeptidase Inhibitors
  作者：Elina M. Jarho、Jarkko I. Venäläinen、Juhani Huuskonen、Johannes A. M. Christiaans、J. Arturo Garcia-Horsman、Markus M. Forsberg、Tomi Järvinen、Jukka Gynther、Pekka T. Männistö、Erik A. A. Wallén

  DOI：10.1021/jm049503w

  日期：2004.11.1

  With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.