2-(4-methoxybenzylidene)-N-((1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)hydrazinecarboxamide | 1416358-67-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-methoxybenzylidene)-N-((1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)hydrazinecarboxamide
• CAS: 1416358-67-2
• 化学式: C₁₉H₂₇N₃O₂
• 分子量: 329.442
• InChiKey: AFHQTEFNBGLRNI-URLQWDBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.72
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-(4-chloro-3-methylphenyl)prop-2-en-1-one 、 2-(4-methoxybenzylidene)-N-((1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)hydrazinecarboxamide 在 polystyrene-supported TBD 、 Amberlyst A-15 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以65.2 mg的产率得到4-benzyl-3-(4-chloro-3-methylphenyl)-N-(1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands

  摘要：

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.031
• 作为产物：
  描述：

  在 肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(4-methoxybenzylidene)-N-((1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)hydrazinecarboxamide
  参考文献：
  名称：

  Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands

  摘要：

  In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available hydrazones and enones (two or three steps). Making use of a mixture of resin supported reagents strategy an efficient domino process allowed the easy construction of various dihydropyrazoles in 63-83% yields. The obtained family of pyrazolines featured significant hCB(2)/hCB(1) selectivity in favor of hCB(2) receptors while more than 1000-3000 nM affinity was only measured for hCB(1) receptors. This is closely related to pyrazole SR144528 inverse agonist/antagonist, although a partial agonist behavior in the [S-35]-GTP gamma S binding assay was mainly measured in our case pointing out a functional switch in action. Furthermore, this hCB(2) selectivity is unique within the pyrazoline CB ligands although the affinity ranging from 251 to 689 nM remains to be improved which give, however, an opportunity for further structure activity relationship. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.031