4-(4-cyanophenyl)-2-(3-chloropropyl)phthalazin-1(2H)-one | 1354720-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-cyanophenyl)-2-(3-chloropropyl)phthalazin-1(2H)-one
• 英文别名: 4-[3-(3-Chloropropyl)-4-oxophthalazin-1-yl]benzonitrile；4-[3-(3-chloropropyl)-4-oxophthalazin-1-yl]benzonitrile
• CAS: 1354720-55-0
• 化学式: C₁₈H₁₄ClN₃O
• 分子量: 323.782
• InChiKey: ZNRFOCPBNQOISW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-(piperidin-4-yl)phenyl]-acetamide 、 4-(4-cyanophenyl)-2-(3-chloropropyl)phthalazin-1(2H)-one 在 sodium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以48%的产率得到4-(4-cyanophenyl)-2-[3-[4-[3-(acetylamino)phenyl]piperidin-1-yl]propyl]phthalazin-1(2H)-one
  参考文献：
  名称：

  4-Arylphthalazin-1(2H)-one derivatives as potent antagonists of the melanin concentrating hormone receptor 1 (MCH-R1)

  摘要：

  A novel series of 4-arylphthalazin-1(2H)-one linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of an extensive SAR study probing the effects of substituents on the 4-arylphthalazin-1(2H)-one C-4 aryl group led to the identification of the 4-(3,4-difluorophenyl) derivative as a highly potent MCH-R1 inhibitor with an IC50 = 1 nM. However, further investigations showed that this substance has unacceptable pharmacokinetic properties including a high clearance and volume of distribution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.111
• 作为产物：
  描述：

  1-氯-3-碘丙烷 、 4-(4-oxo-3H-phthalazin-1-yl)benzonitrile 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 4-(4-cyanophenyl)-2-(3-chloropropyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  4-Arylphthalazin-1(2H)-one derivatives as potent antagonists of the melanin concentrating hormone receptor 1 (MCH-R1)

  摘要：

  A novel series of 4-arylphthalazin-1(2H)-one linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of an extensive SAR study probing the effects of substituents on the 4-arylphthalazin-1(2H)-one C-4 aryl group led to the identification of the 4-(3,4-difluorophenyl) derivative as a highly potent MCH-R1 inhibitor with an IC50 = 1 nM. However, further investigations showed that this substance has unacceptable pharmacokinetic properties including a high clearance and volume of distribution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.111