4-Cyclohexyliminomethyleneamino-N-[2-(2,4-dichloro-phenyl)-ethyl]-benzamide | 1025983-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Cyclohexyliminomethyleneamino-N-[2-(2,4-dichloro-phenyl)-ethyl]-benzamide
• 英文别名: 4-(cyclohexyliminomethylideneamino)-N-[2-(2,4-dichlorophenyl)ethyl]benzamide
• CAS: 1025983-84-9
• 化学式: C₂₂H₂₃Cl₂N₃O
• 分子量: 416.35
• InChiKey: UFVPBLJOCZMWES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-哌嗪酮 、 4-Cyclohexyliminomethyleneamino-N-[2-(2,4-dichloro-phenyl)-ethyl]-benzamide 以 四氢呋喃 为溶剂， 反应 2.0h， 以73 mg的产率得到(4-{[(1Z)-2-aza-2-cyclohexyl-1-(3-oxopiperazinyl)vinyl]amino}phenyl)-N-[2-(2,4-dichlorophenyl)ethyl]carboxamide
  参考文献：
  名称：

  Phenylguanidines as Selective Nonpeptide Melanocortin-5 Receptor Antagonists

  摘要：

  A series of phenylguanidine analogues represented by 10, 12, and 21 were synthesized and found to have high binding affinities for the human melanocortin-5 receptor. Their binding affinities for three other melanocortin receptor subtypes, MC1, MC3, and MC4, were low. Selected compounds were also tested for their functional activity and exhibited inhibition of cc-MSH-stimulated cAMP production in cells expressing the human MC5 receptor. Compound 10 had a K-j value of 2.1 nM in the binding assay and an IC50 of 72 nM in the functional assay. Some analogues such as 13 from this series possessed weak agonist activity at the human MC4 receptor.

  DOI：

  10.1021/jm0400496
• 作为产物：
  描述：

  2,4-二氯苯酚呋喃 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 4-Cyclohexyliminomethyleneamino-N-[2-(2,4-dichloro-phenyl)-ethyl]-benzamide
  参考文献：
  名称：

  Phenylguanidines as Selective Nonpeptide Melanocortin-5 Receptor Antagonists

  摘要：

  A series of phenylguanidine analogues represented by 10, 12, and 21 were synthesized and found to have high binding affinities for the human melanocortin-5 receptor. Their binding affinities for three other melanocortin receptor subtypes, MC1, MC3, and MC4, were low. Selected compounds were also tested for their functional activity and exhibited inhibition of cc-MSH-stimulated cAMP production in cells expressing the human MC5 receptor. Compound 10 had a K-j value of 2.1 nM in the binding assay and an IC50 of 72 nM in the functional assay. Some analogues such as 13 from this series possessed weak agonist activity at the human MC4 receptor.

  DOI：

  10.1021/jm0400496

文献信息

• Phenylguanidines as Selective Nonpeptide Melanocortin-5 Receptor Antagonists
  作者：Chen、Jinghua Yu、Beth A. Fleck、Sam R. J. Hoare、John Saunders、Alan C. Foster

  DOI：10.1021/jm0400496

  日期：2004.7.1

  A series of phenylguanidine analogues represented by 10, 12, and 21 were synthesized and found to have high binding affinities for the human melanocortin-5 receptor. Their binding affinities for three other melanocortin receptor subtypes, MC1, MC3, and MC4, were low. Selected compounds were also tested for their functional activity and exhibited inhibition of cc-MSH-stimulated cAMP production in cells expressing the human MC5 receptor. Compound 10 had a K-j value of 2.1 nM in the binding assay and an IC50 of 72 nM in the functional assay. Some analogues such as 13 from this series possessed weak agonist activity at the human MC4 receptor.