1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid | 746661-99-4

• 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-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid
• 英文别名: 3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-(3,4,5-trimethoxyanilino)benzimidazole-5-carboxylic acid
• CAS: 746661-99-4
• 化学式: C₂₅H₃₂N₄O₇
• 分子量: 500.552
• InChiKey: MQSMWWPVWHFKNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid 、 二异丁胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 3-{6-[(diisobutylamino)carbonyl]-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazol-1-yl}propylcarbamate
  参考文献：
  名称：

  Identification of a novel series of benzimidazoles as potent and selective antagonists of the human melanocortin-4 receptor

  摘要：

  A novel series of benzimidazoles was identified and optimized, leading to the discovery of potent and selective antagonists of the human melanocortin-4 receptor. In addition, compound 5i was shown to cross the blood-brain barrier after intravenous dosing in rats. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.010
• 作为产物：
  描述：

  methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以93%的产率得到1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid
  参考文献：
  名称：

  Novel derivatives of benzimidazole and imidazo-pyridine and their use as medicaments

  摘要：

  具有以下结构的化合物及其药用盐具有良好的亲和力，适用于治疗包括疼痛、炎症等在内的疾病，其中取代基如规范中所定义的亚型黑素皮质激素受体。

  公开号：

  US20050065179A1

文献信息

• Novel benzimidazole and imidazopyridine derivatives and use thereof as a medicament
  申请人：Poitout Lydie

  公开号：US20050267147A1

  公开（公告）日：2005-12-01

  A compound of the formula wherein the substituents are as defined in the specification and pharmaceutical salts thereof having a good affinity for sub-types of melanocortin receptors making them useful for treating diseases in which such receptors are included such as pain, inflammatory conditions, etc.

  该化合物的化学式为，在该化学式中，取代基的定义如规范中所述，其药物盐具有良好的亲和力，可用于治疗包含此类受体的疾病，例如疼痛、炎症等。
• NOVEL DERIVATIVES OF BENZIMIDAZOLE AND IMIDAZO-PYRIDINE AND THEIR USE AS MEDICAMENTS
  申请人：POITOUT Lydie

  公开号：US20090270372A1

  公开（公告）日：2009-10-29

  A subject of the present Application is novel derivatives of benzimidazole and imidazopyridine which have a good affinity for certain sub-types of melanocortin receptors, in particular the MC4 receptors. They are particularly useful for treating pathological conditions and diseases in which one or more melanocortin receptors are involved. The invention also relates to pharmaceutical compositions containing said products.

  本申请的主题是苯并咪唑和咪唑吡啶的新衍生物，它们对于某些亚型的黑色素皮质素受体，特别是MC4受体具有良好的亲和力。它们特别适用于治疗涉及一个或多个黑色素皮质素受体的病理条件和疾病。本发明还涉及含有上述产物的制药组合物。
• Novel derivatives of benzimidazale and imidazo-pyridine and their use as medicaments
  申请人：Poitout Lydie

  公开号：US20080139619A1

  公开（公告）日：2008-06-12

  A subject of the present application is novel derivatives of benzimidazole and imidazo-pyridine which have a good affinity for certain sub-types of melanocortin receptors, in particular the MC4 receptors. They are particularly useful for treating pathological conditions and diseases in which one or more melanocortin receptors are involved. The invention also relates to pharmaceutical compositions containing said products.

  本申请的主题是苯并咪唑和咪唑吡啶的新衍生物，它们对于某些亚型的黑素皮质素受体，特别是MC4受体具有良好的亲和力。它们特别适用于治疗涉及一个或多个黑素皮质素受体的病理条件和疾病。本发明还涉及含有上述产品的制药组合物。
• Benzimidazole and imidazopyridine derivatives and use thereof as a medicament
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US07355052B2

  公开（公告）日：2008-04-08

  A compound of the formula wherein the substituents are as defined in the specification and pharmaceutical salts thereof having a good affinity for sub-types of melanocortin receptors making them useful for treating diseases in which such receptors are included such as pain, inflammatory conditions, etc.

  一种化合物，其化学式如下，其中取代基如规范中所定义，并且具有良好的亚型黑素皮质素受体亲和力的药物盐，使其可用于治疗包括疼痛、炎症等疾病的亚型黑素皮质素受体的相关疾病。
• Derivatives of benzimidazole and imidazo-pyridine and their use as medicaments
  申请人：Ipsen Pharma S.A.S.

  公开号：US07816539B2

  公开（公告）日：2010-10-19

  A subject of the present Application is novel derivatives of benzimidazole and imidazopyridine which have a good affinity for certain sub-types of melanocortin receptors, in particular the MC4 receptors. They are particularly useful for treating pathological conditions and diseases in which one or more melanocortin receptors are involved. The invention also relates to pharmaceutical compositions containing said products.

  本申请的主题是苯并咪唑和咪唑吡啶的新型衍生物，它们具有良好的亲和力，特别是对MC4受体的某些亚型。它们特别适用于治疗其中一个或多个黑色素皮质素受体参与的病理条件和疾病。本发明还涉及含有所述产品的制药组合物。