2-(4-Carboxyphenyl)-4-methylbenzimidazole

• 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: 2-(4-Carboxyphenyl)-4-methylbenzimidazole
• 英文别名: 4-(4-methyl-1H-benzimidazol-2-yl)benzoic acid
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD11849229
• 分子量: 252.272
• InChiKey: JEWNCLFMXLNQIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Carboxyphenyl)-4-methylbenzimidazole 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-methyl-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
• 作为产物：
  描述：

  对醛基苯甲酸 、 2,3-二氨基甲苯 以 硝基苯 为溶剂， 生成 2-(4-Carboxyphenyl)-4-methylbenzimidazole
  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

• Methods for the solid phase synthesis of combinatorial libraries of benzimidazol, benzoxazoles, benzothiazoles, and derivatives thereof
  申请人：——

  公开号：US20010024833A1

  公开（公告）日：2001-09-27

  The present invention provides an efficient and versatile method for the synthesis and screening of combinatorial libraries of benzimidazoles, benzoxazoles, benzothiazoles, and derivatives thereof. In order to expedite the synthesis of large arrays of compounds possessing these core structures, a general methodology for solid phase synthesis of these derivatives is provided. Arrays of benzimidazoles, benzoxazoles, benzothiazoles, and derivatives thereof useful as peptidomimetics and for the identification of agents having antifungal, antiviral, antimicrobial, anticoagulant, and antiulcer activity, or use in the treatment of inflammation, hypertension, cancer, and other conditions can be prepared by this method.

  本发明提供了一种高效且多功能的方法，用于合成和筛选苯并咪唑，苯并噁唑，苯并噻唑及其衍生物的组合库。为了加速合成具有这些核心结构的大量化合物，提供了一种这些衍生物的固相合成的通用方法。通过这种方法可以制备苯并咪唑，苯并噁唑，苯并噻唑及其衍生物的数组，这些数组可用作肽类模拟物，并用于鉴定具有抗真菌，抗病毒，抗微生物，抗凝血和抗溃疡活性或用于治疗炎症，高血压，癌症和其他疾病的药物。
• US6251689B1
  申请人：——

  公开号：US6251689B1

  公开（公告）日：2001-06-26
• 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.