1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(7-methoxy-1H-benzoimidazol-2-yl)-phenyl]-urea

• 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: 1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(7-methoxy-1H-benzoimidazol-2-yl)-phenyl]-urea
• 英文别名: 1-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-3-(4-(7-methoxy-1H-benzo[d]imidazol-2-yl)phenyl)urea；1-[4-(1H-benzimidazol-2-yl)phenyl]-3-[4-(4-methoxy-1H-benzimidazol-2-yl)phenyl]urea
• 化学式: C₂₈H₂₂N₆O₂
• 分子量: 474.522
• InChiKey: QYSVQVPQJCWZJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(7-methoxy-1H-benzoimidazol-2-yl)-benzoic acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 生成 1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(7-methoxy-1H-benzoimidazol-2-yl)-phenyl]-urea
  参考文献：
  名称：

  1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors

  摘要：

  A novel class of 1-[4-(1H-benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-ureas are described as potent inhibitors of heparanase. Among them are 1,3-bis-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea (7a) and 1,3-bis-[4-(5,6-dimethyl-1H-benzoimidazol-2-yl)-phenyl]-urea (7d), which displayed good heparanase inhibitory activity (IC50 0.075-0.27 mu M). Compound 7a showed good efficacy in a B16 metastasis model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.069

文献信息

• [EN] (BENZIMIDAZOL-2-YL)-PHENYL-PHENYL-UREA COMPOUNDS AND METHODS FOR INHIBITING HEPARANASE ACTIVITY<br/>[FR] COMPOSES DE (BENZIMIDAZOL-2-YL)-PHENYL-PHENYL-UREE ET PROCEDES D'INHIBITION DE L'ACTIVITE DE L'HEPARANASE
  申请人：IMCLONE SYSTEMS INC

  公开号：WO2005042495A1

  公开（公告）日：2005-05-12

  The present invention encompasses heparanase inhibitors, particularly to certain (benzimidazol-2-yl)-phenyl-phenyl-urea derivatives that inhibit heparanase, pharmaceutical compositions that contain the compounds, methods for making the compounds, and methods of treating heparanase-dependent diseases and conditions in mammals by administering a therapeutically effective amount of the compounds to the mammals.

  本发明涉及抑制肝素酶的抑制剂，特别是某些（苯并咪唑-2-基）-苯基-苯基-脲衍生物，这些衍生物可以抑制肝素酶，以及包含这些化合物的制药组合物，制备这些化合物的方法，以及通过向哺乳动物施用治疗有效量的这些化合物来治疗肝素酶依赖性疾病和病况的方法。
• 1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors
  作者：Weitao Pan、Hua-Quan Miao、Yong-Jiang Xu、Elizabeth C. Navarro、James R. Tonra、Erik Corcoran、Armin Lahiji、Paul Kussie、Alexander S. Kiselyov、Wai C. Wong、Hu Liu

  DOI：10.1016/j.bmcl.2005.09.069

  日期：2006.1

  A novel class of 1-[4-(1H-benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-ureas are described as potent inhibitors of heparanase. Among them are 1,3-bis-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea (7a) and 1,3-bis-[4-(5,6-dimethyl-1H-benzoimidazol-2-yl)-phenyl]-urea (7d), which displayed good heparanase inhibitory activity (IC50 0.075-0.27 mu M). Compound 7a showed good efficacy in a B16 metastasis model. (c) 2005 Elsevier Ltd. All rights reserved.