(+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid methyl ester | 277751-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid methyl ester
• 英文别名: (+/-)-2-benzylaminocarbonyl-2-cyclopentene-1-carboxylic acid methyl ester；2-(benzylcarbamomoyl)-cyclopent-2-ene-carboxylic acid methyl ester；2-(Benzylcarbamoyl)-cyclopent-2-ene-carboxylic acid methyl ester；methyl 2-(benzylcarbamoyl)cyclopent-2-ene-1-carboxylate
• CAS: 277751-26-5
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: UJEDKGJALATKHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 (+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  New Proline Mimetics:  Synthesis of Thrombin Inhibitors Incorporating Cyclopentane- and Cyclopentenedicarboxylic Acid Templates in the P2 Position. Binding Conformation Investigated by X-ray Crystallography

  摘要：

  With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).

  DOI：

  10.1021/jm990557t
• 作为产物：
  描述：

  7,7-二氯二环[3.2.0]庚-2-烯-6-酮 在 sodium chlorite 、 sodium dihydrogenphosphate 、 碳酸氢钠 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 间苯二酚 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 10.0h， 生成 (+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  New Proline Mimetics:  Synthesis of Thrombin Inhibitors Incorporating Cyclopentane- and Cyclopentenedicarboxylic Acid Templates in the P2 Position. Binding Conformation Investigated by X-ray Crystallography

  摘要：

  With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).

  DOI：

  10.1021/jm990557t

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。
• [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：WO2004060862A3

  公开（公告）日：2004-11-25
• COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY
  申请人：Orion Corporation

  公开号：EP1581489A2

  公开（公告）日：2005-10-05
• 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.
• New Proline Mimetics:  Synthesis of Thrombin Inhibitors Incorporating Cyclopentane- and Cyclopentenedicarboxylic Acid Templates in the P2 Position. Binding Conformation Investigated by X-ray Crystallography
  作者：Daniel Nöteberg、Jonas Brånalt、Ingemar Kvarnström、Marcel Linschoten、Djordje Musil、Jan-Erik Nyström、Guido Zuccarello、Bertil Samuelsson

  DOI：10.1021/jm990557t

  日期：2000.5.1

  With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).