5-(1H-pyrazol-3-yl)pentanoic acid | 93048-15-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(1H-pyrazol-3-yl)pentanoic acid
• 英文别名: 5-(1(2)H-pyrazol-3-yl)-pentanoic acid；5--valeriansaeure
• CAS: 93048-15-8
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: OORNKTYOYYLSGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.98
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(茚满-2-基)-5,6,7,8-四氢吡啶并[4,3-D]嘧啶-2-胺 、 5-(1H-pyrazol-3-yl)pentanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以12%的产率得到1-(2-((2,3-dihydro-1H-inden-2-yl)amino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-(1H-pyrazol-3-yl)pentan-1-one
  参考文献：
  名称：

  Novel Autotaxin Inhibitors for the Treatment of Osteoarthritis Pain: Lead Optimization via Structure-Based Drug Design

  摘要：

  In an effort to develop a novel therapeutic agent aimed at addressing the unmet need of patients with osteoarthritis pain, we set out to develop an inhibitor for autotaxin with excellent potency and physical properties to allow for the clinical investigation of autotaxin-induced nociceptive and neuropathic pain. An initial hit identification campaign led to an aminopyrimidine series with an autotaxin IC50 of 500 nM. X-ray crystallography enabled the optimization to a lead compound that demonstrated favorable potency (IC50 = 2 nM), PK properties, and a robust PK/PD relationship.

  DOI：

  10.1021/acsmedchemlett.6b00207
• 作为产物：
  描述：

  benzyl 5-(1H-pyrazol-3-yl)pent-4-ynoate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以67%的产率得到5-(1H-pyrazol-3-yl)pentanoic acid
  参考文献：
  名称：

  Novel Autotaxin Inhibitors for the Treatment of Osteoarthritis Pain: Lead Optimization via Structure-Based Drug Design

  摘要：

  In an effort to develop a novel therapeutic agent aimed at addressing the unmet need of patients with osteoarthritis pain, we set out to develop an inhibitor for autotaxin with excellent potency and physical properties to allow for the clinical investigation of autotaxin-induced nociceptive and neuropathic pain. An initial hit identification campaign led to an aminopyrimidine series with an autotaxin IC50 of 500 nM. X-ray crystallography enabled the optimization to a lead compound that demonstrated favorable potency (IC50 = 2 nM), PK properties, and a robust PK/PD relationship.

  DOI：

  10.1021/acsmedchemlett.6b00207