N-(2-{4-[(R)-2-Amino-3-(4-chloro-phenyl)-propionyl]-piperazin-1-yl}-phenyl)-N-methyl-methanesulfonamide | 850998-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-(2-{4-[(R)-2-Amino-3-(4-chloro-phenyl)-propionyl]-piperazin-1-yl}-phenyl)-N-methyl-methanesulfonamide
• CAS: 850998-14-0
• 化学式: C₂₁H₂₇ClN₄O₃S
• 分子量: 450.989
• InChiKey: MSUNTJKXXAXHHZ-GOSISDBHSA-N

物化性质

• 沸点：
  645.3±65.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(2-{4-[(R)-2-Amino-3-(4-chloro-phenyl)-propionyl]-piperazin-1-yl}-phenyl)-N-methyl-methanesulfonamide 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 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid ((R)-1-(4-chloro-benzyl)-2-{4-[2-(methanesulfonyl-methyl-amino)-phenyl]-piperazin-1-yl}-2-oxo-ethyl)-amide
  参考文献：
  名称：

  Melanocortin subtype-4 receptor agonists containing a piperazine core with substituted aryl sulfonamides

  摘要：

  The biological activity for a set of melanocortin-4 receptor (MC4R) agonists containing a piperazine core with an ortho-substituted aryl sulfonamide is described. Compounds from this set had binding and functional activities at MC4R less than 30 nM. The most selective compound in this series was > 25,000-fold more potent at MC4R than MC3R, and 490-fold more potent at MC4R than MC5R. This compound also reduced food intake after oral dosing at 25, 50, and 100 mg kg(-1) in fasted mice. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.060
• 作为产物：
  描述：

  1-tert-butoxycarbonyl-4-(2-((methylsulfonyl)amino)phenyl)piperazine 在 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-{4-[(R)-2-Amino-3-(4-chloro-phenyl)-propionyl]-piperazin-1-yl}-phenyl)-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Melanocortin subtype-4 receptor agonists containing a piperazine core with substituted aryl sulfonamides

  摘要：

  The biological activity for a set of melanocortin-4 receptor (MC4R) agonists containing a piperazine core with an ortho-substituted aryl sulfonamide is described. Compounds from this set had binding and functional activities at MC4R less than 30 nM. The most selective compound in this series was > 25,000-fold more potent at MC4R than MC3R, and 490-fold more potent at MC4R than MC5R. This compound also reduced food intake after oral dosing at 25, 50, and 100 mg kg(-1) in fasted mice. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.060