1,3-diethyl-2-<3-(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide | 139167-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-diethyl-2-<3-(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide
• 英文别名: 1,3-diethyl-2-[(E,3Z)-3-(1-ethyl-3,3-dimethylindol-2-ylidene)prop-1-enyl]benzo[f]benzimidazol-3-ium;iodide
• CAS: 139167-44-5
• 化学式: C₃₀H₃₄N₃*I
• 分子量: 563.525
• InChiKey: AQGGEJMIRFQKAE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.05
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,3-diethyl-2-<3-(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide 在 amberlite IRA-400 chloride ion-exchange resin 作用下， 反应 2.0h， 以88.2%的产率得到1,3-diethyl-2-<3-(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium chloride
  参考文献：
  名称：

  Synthesis and substance P antagonist activity of naphthimidazolium derivatives

  摘要：

  The synthesis of unsymmetrical naphth[2,3-d]imidazolium and bridged naphth[2,3-d]imidazolium derivatives and their substance P (SP) antagonist activity are described. All compounds were evaluated for their ability to displace SP from neurokinin-1 (NK-1) receptor sites using standard receptor binding methodology (rat forebrain membrane). 1,3-Diethyl-2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-1H-naphth[2,3-d]imidazolium chloride (7a), a representative compound in this series, was further evaluated for SP antagonist activity in a guinea pig ileum contractility assay. In vivo SP antagonist activity of 7a was demonstrated using SP-induced salivation and paw edema models performed in rats.

  DOI：

  10.1021/jm00085a015
• 作为产物：
  描述：

  1-ethyl-2-methyl-1H-naphth<2,3-d>imidazole 在 乙酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 9.5h， 生成 1,3-diethyl-2-<3-(1,3-dihydro-3,3-dimethyl-1-ethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide
  参考文献：
  名称：

  Synthesis and substance P antagonist activity of naphthimidazolium derivatives

  摘要：

  The synthesis of unsymmetrical naphth[2,3-d]imidazolium and bridged naphth[2,3-d]imidazolium derivatives and their substance P (SP) antagonist activity are described. All compounds were evaluated for their ability to displace SP from neurokinin-1 (NK-1) receptor sites using standard receptor binding methodology (rat forebrain membrane). 1,3-Diethyl-2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-1H-naphth[2,3-d]imidazolium chloride (7a), a representative compound in this series, was further evaluated for SP antagonist activity in a guinea pig ileum contractility assay. In vivo SP antagonist activity of 7a was demonstrated using SP-induced salivation and paw edema models performed in rats.

  DOI：

  10.1021/jm00085a015