2-{1-[(1-Benzyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-cyclopentylmethyl}-pentanoic acid tert-butyl ester | 906069-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-{1-[(1-Benzyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-cyclopentylmethyl}-pentanoic acid tert-butyl ester
• CAS: 906069-99-6
• 化学式: C₂₈H₃₈N₂O₄
• 分子量: 466.621
• InChiKey: DFYPPLJGHSNINE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.4
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{1-[(1-Benzyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-cyclopentylmethyl}-pentanoic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以63%的产率得到2-{1-[(1-Benzyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-cyclopentylmethyl}-pentanoic acid
  参考文献：
  名称：

  Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides

  摘要：

  Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)

  DOI：

  10.1021/jm060133g
• 作为产物：
  描述：

  1-(2-tert-butoxycarbonyl-pent-4-enyl)cyclopentanecarboxylic acid 在 palladium on activated charcoal 二苯基磷酸 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 24.5h， 生成 2-{1-[(1-Benzyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-cyclopentylmethyl}-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides

  摘要：

  Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)

  DOI：

  10.1021/jm060133g