5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-methyl-2-nitroaniline | 1140503-26-9

• 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-methyl-2-nitroaniline
• CAS: 1140503-26-9
• 化学式: C₂₉H₃₄N₆O₂
• 分子量: 498.628
• InChiKey: OHMWCLQCLAROLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  90.33
• 氢给体数：
  2.0
• 氢受体数：
  6.0

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-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
• 作为产物：
  描述：

  2-(4-tert-butylphenyl)-4-[4-(3-fluoro-4-nitrobenzyl)piperazin-1-yl]-1H-benzimidazole 、 甲胺 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以95%的产率得到5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)-N-methyl-2-nitroaniline
  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