(1R)-2-piperidinylcarbonyl-2-cyclopentene-1-carboxylic acid methyl ester | 277751-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R)-2-piperidinylcarbonyl-2-cyclopentene-1-carboxylic acid methyl ester
• 英文别名: methyl (1R)-2-(piperidine-1-carbonyl)cyclopent-2-ene-1-carboxylate
• CAS: 277751-28-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: IOZAMCJQWWRIPK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-2-piperidinylcarbonyl-2-cyclopentene-1-carboxylic acid methyl ester 在 sodium hydroxide 、 三氟甲磺酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (R)-2-(Piperidine-1-carbonyl)-cyclopent-2-enecarboxylic acid 4-carbamimidoyl-benzylamide
  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 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 碳酸氢钠 、 对甲苯磺酸 、 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 (1R)-2-piperidinylcarbonyl-2-cyclopentene-1-carboxylic 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

• 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).