N-(2-chloroethyl)-2-(3-methoxyphenyl)-2-(p-tolyl)hydrazine-1-carboxamide | 869005-04-9

• 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: N-(2-chloroethyl)-2-(3-methoxyphenyl)-2-(p-tolyl)hydrazine-1-carboxamide
• CAS: 869005-04-9
• 化学式: C₁₇H₂₀ClN₃O₂
• 分子量: 333.818
• InChiKey: LMDZUXGOVVYGON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  53.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-chloroethyl)-2-(3-methoxyphenyl)-2-(p-tolyl)hydrazine-1-carboxamide 在 水 作用下， 以 甲醇 为溶剂， 以40%的产率得到2-(4,5-Dihydro-1,3-oxazol-2-yl)-1-(3-methoxyphenyl)-1-(4-methylphenyl)hydrazine
  参考文献：
  名称：

  Bioisosteric phentolamine analogs as potent α-adrenergic antagonists

  摘要：

  The synthesis and biological evaluation of a new series of bioisosteric phentolamine analogs are described. Replacement of the carbon next to the imidazoline ring of phentolamine with a nitrogen atom provides compounds (2, 3) that are about 1.6 times and 4.1 times more potent functionally than phentolamine on rat alpha(1)-adrenergic receptors, respectively. In receptor binding assays, the affinities of phentolamine and its bioisosteric analogs were determined on the human embryonic kidney (HEK) and Chinese Hamster ovary (CHO) cell lines expressing the human alpha(1)- and alpha(2)-AR subtypes, respectively. Analogs 2 and 3, both, displayed higher binding affinities at the alpha(2)- versus the alpha(1)-ARs, affinities being the least at the alpha(1B)-AR. Binding affinities of the methoxy ether analog 2 were greater than those of the phenolic analog 3 at all six alpha-AR subtypes. One of the nitrogen atoms in the imidazoline ring of phentolamine was replaced with an oxygen atom to give compounds 4 and 5, resulting in a 2-substituted oxazoline ring. The low functional antagonist activity on rat aorta, and binding potencies of these two compounds on human alpha(1A)- and alpha(2A)-AR subtypes indicate that a basic functional group is important for optimum binding to the alpha(1)- and alpha(2A)-adrenergic receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.083
• 作为产物：
  描述：

  对甲基间羟基二苯胺 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 5.0h， 生成 N-(2-chloroethyl)-2-(3-methoxyphenyl)-2-(p-tolyl)hydrazine-1-carboxamide
  参考文献：
  名称：

  Bioisosteric phentolamine analogs as potent α-adrenergic antagonists

  摘要：

  The synthesis and biological evaluation of a new series of bioisosteric phentolamine analogs are described. Replacement of the carbon next to the imidazoline ring of phentolamine with a nitrogen atom provides compounds (2, 3) that are about 1.6 times and 4.1 times more potent functionally than phentolamine on rat alpha(1)-adrenergic receptors, respectively. In receptor binding assays, the affinities of phentolamine and its bioisosteric analogs were determined on the human embryonic kidney (HEK) and Chinese Hamster ovary (CHO) cell lines expressing the human alpha(1)- and alpha(2)-AR subtypes, respectively. Analogs 2 and 3, both, displayed higher binding affinities at the alpha(2)- versus the alpha(1)-ARs, affinities being the least at the alpha(1B)-AR. Binding affinities of the methoxy ether analog 2 were greater than those of the phenolic analog 3 at all six alpha-AR subtypes. One of the nitrogen atoms in the imidazoline ring of phentolamine was replaced with an oxygen atom to give compounds 4 and 5, resulting in a 2-substituted oxazoline ring. The low functional antagonist activity on rat aorta, and binding potencies of these two compounds on human alpha(1A)- and alpha(2A)-AR subtypes indicate that a basic functional group is important for optimum binding to the alpha(1)- and alpha(2A)-adrenergic receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.083