Methyl 3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridine-2-carboxylate | 1448862-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridine-2-carboxylate
• 英文别名: methyl 3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate
• CAS: 1448862-60-9
• 化学式: C₉H₁₁ClN₂O₂
• 分子量: 214.652
• InChiKey: QEBDHEBHIROSFE-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氰-2-甲基吡啶 、 Methyl 3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridine-2-carboxylate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 6-[2-(3-Chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-2-oxoethyl]pyridine-3-carbonitrile
  参考文献：
  名称：

  A novel series of metabotropic glutamate receptor 5 negative allosteric modulators based on a 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine core

  摘要：

  A series of potent non-acetylinic negative allosteric modulators of the metabotropic glutamate receptor 5 (mGlu5 NAMs) was developed starting from HTS screening hit 1. Potency was improved via iterative SAR, and physicochemical properties were optimized to deliver orally bioavailable compounds acceptable for in vivo testing. A lead molecule from the series demonstrated dose-dependent activity in the second phase of the rat formalin test from 30 mg/kg, and a preliminary PK/PD relationship was established. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.044
• 作为产物：
  描述：

  methyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 Methyl 3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridine-2-carboxylate
  参考文献：
  名称：

  A novel series of metabotropic glutamate receptor 5 negative allosteric modulators based on a 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine core

  摘要：

  A series of potent non-acetylinic negative allosteric modulators of the metabotropic glutamate receptor 5 (mGlu5 NAMs) was developed starting from HTS screening hit 1. Potency was improved via iterative SAR, and physicochemical properties were optimized to deliver orally bioavailable compounds acceptable for in vivo testing. A lead molecule from the series demonstrated dose-dependent activity in the second phase of the rat formalin test from 30 mg/kg, and a preliminary PK/PD relationship was established. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.044