5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-1-methylbenzene-1,2-diamine | 1140503-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-1-methylbenzene-1,2-diamine
• CAS: 1140503-27-0
• 化学式: C₂₉H₃₆N₆
• 分子量: 468.645
• InChiKey: DGULVFSUXFSFTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  73.21
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-1-methylbenzene-1,2-diamine 、 草酰基二咪唑 以 四氢呋喃 为溶剂， 以40%的产率得到7-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-1-methylquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Discovery of 6-({4-[2-(4-tert-Butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): An Orally Active Antagonist of the Gonadotropin Releasing Hormone Receptor (GnRH-R)

  摘要：

  A potent, highly insoluble, GnRH antagonist with a 2-phenyl-4-piperazinylbenzimidazole template and a quinoxaline-2,3-dione pharmacophore was modified to maintain GnRH antagonist activity and improve in vitro pharmaceutical properties. Structural changes to the quinoxaline-2,3-dione portion of the molecule resulted in several structures with improved properties and culminated in the discovery of 6-((4-[2-(4-tertbutylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024). The compound was shown to have excellent pharmacokinetic parameters and lowered rat plasma LH levels after oral administration.

  DOI：

  10.1021/jm801572m
• 作为产物：
  描述：

  5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-methyl-2-nitroaniline 在 platinum on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-1-methylbenzene-1,2-diamine
  参考文献：
  名称：

  Discovery of 6-({4-[2-(4-tert-Butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): An Orally Active Antagonist of the Gonadotropin Releasing Hormone Receptor (GnRH-R)

  摘要：

  A potent, highly insoluble, GnRH antagonist with a 2-phenyl-4-piperazinylbenzimidazole template and a quinoxaline-2,3-dione pharmacophore was modified to maintain GnRH antagonist activity and improve in vitro pharmaceutical properties. Structural changes to the quinoxaline-2,3-dione portion of the molecule resulted in several structures with improved properties and culminated in the discovery of 6-((4-[2-(4-tertbutylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024). The compound was shown to have excellent pharmacokinetic parameters and lowered rat plasma LH levels after oral administration.

  DOI：

  10.1021/jm801572m