1-(4-chloro-3-methylphenyl)-2-methyleneheptan-1-one | 1416358-63-8

• 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: 1-(4-chloro-3-methylphenyl)-2-methyleneheptan-1-one
• 英文别名: 1-(4-Chloro-3-methylphenyl)-2-methylideneheptan-1-one；1-(4-chloro-3-methylphenyl)-2-methylideneheptan-1-one
• CAS: 1416358-63-8
• 化学式: C₁₅H₁₉ClO
• 分子量: 250.768
• InChiKey: FSPIGUMCMSBEQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chloro-3-methylphenyl)-2-methyleneheptan-1-one 、 N-cyclohexyl-2-(4-methoxybenzylidene)hydrazinecarboxamide 在 polystyrene-supported TBD 、 Amberlyst A-15 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以75 mg的产率得到5-(4-chloro-3-methylphenyl)-N-cyclohexyl-4-pentyl-3,4-dihydropyrazole-2-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：

  4-氯-3-甲基苯甲酸 在 哌啶 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-(4-chloro-3-methylphenyl)-2-methyleneheptan-1-one
  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

文献信息

• Scaffold hopping strategy toward original pyrazolines as selective CB2 receptor ligands
  作者：Vincent Gembus、Christophe Furman、Régis Millet、Roxane Mansouri、Philippe Chavatte、Vincent Levacher、Jean-François Brière

  DOI：10.1016/j.ejmech.2012.10.031

  日期：2012.12

  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.