5-({4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline | 874278-30-5

• 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-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline
• 英文别名: 5-((4-(2-(4-tert-butylphenyl)-1H-benzo[d]imidazol-4-yl)piperazin-1-yl)methyl)quinoxaline；5-[[4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl]methyl]quinoxaline
• CAS: 874278-30-5
• 化学式: C₃₀H₃₂N₆
• 分子量: 476.624
• InChiKey: MRIRODCBQYGJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  草酸醛 、 2-amino-3-({4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)phenylamine 以 甲醇 、 水 为溶剂， 反应 18.0h， 以38%的产率得到5-({4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline
  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

文献信息

• Gonadotropin releasing hormone receptor antagonists
  申请人：Garrick Michael Lloyd

  公开号：US20060019965A1

  公开（公告）日：2006-01-26

  The present invention relates to Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.

  本发明涉及促性腺激素释放激素（“GnRH”）（也称为促黄体生成激素释放激素）受体拮抗剂。
• GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS
  申请人：Wyeth

  公开号：EP1758895A1

  公开（公告）日：2007-03-07
• US7696210B2
  申请人：——

  公开号：US7696210B2

  公开（公告）日：2010-04-13
• [EN] GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEURS DE L'HORMONE DE LIBÉRATION DE GONADOTROPHINES
  申请人：WYETH CORP

  公开号：WO2006009734A1

  公开（公告）日：2006-01-26

  The present invention relates to Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.