2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid | 554457-11-3

• 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-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid
• 英文别名: 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acid；1-(3-methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazole-5-carboxylic acid
• CAS: 554457-11-3
• 化学式: C₂₄H₂₈N₄O₃
• 分子量: 420.511
• InChiKey: GUSYHQUUVADYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid 在 lithium aluminium tetrahydride 、 TEA 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester
  参考文献：
  名称：

  Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity

  摘要：

  Extensive SAR studies and optimization of ADME properties of benzimidazol-2-one derivatives led to the identification of BMS-433771 (3) as an orally active RSV fusion inhibitor. In order to extend the structure-activity relationships for this compound series, substitution of the benzimidazole ring was examined with a view to establishing additional productive interactions between the inhibitor and functionality present in the proposed binding pocket. Amongst the compounds synthesized, the 5-aminomethyl analogue 10aa demonstrated potent antiviral activity towards wild-type RSV and retained excellent inhibitory activity towards a virus that had been developed to express resistance to BMS-433771 (3), data consistent with an additional productive interaction between the inhibitor and the fusion protein target. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.102
• 作为产物：
  描述：

  异戊胺 在 palladium on activated charcoal sodium hydroxide 、 氯化亚砜 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity

  摘要：

  Extensive SAR studies and optimization of ADME properties of benzimidazol-2-one derivatives led to the identification of BMS-433771 (3) as an orally active RSV fusion inhibitor. In order to extend the structure-activity relationships for this compound series, substitution of the benzimidazole ring was examined with a view to establishing additional productive interactions between the inhibitor and functionality present in the proposed binding pocket. Amongst the compounds synthesized, the 5-aminomethyl analogue 10aa demonstrated potent antiviral activity towards wild-type RSV and retained excellent inhibitory activity towards a virus that had been developed to express resistance to BMS-433771 (3), data consistent with an additional productive interaction between the inhibitor and the fusion protein target. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.102

文献信息

• Novel use of phenylheteroakylamine derivatives
  申请人：——

  公开号：US20030158185A1

  公开（公告）日：2003-08-21

  There is disclosed the use of a compound of formula (I) wherein R 1 , R 2 , X, Y, V, W and Z are as defined in the specification, and pharmaceutically acceptable salts, enantiomers or racemates thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of nitric oxide synthase activity is beneficial. Certain novel compounds of formula (Ia) and pharmaceutically acceptable salts thereof, and enantiomers and racemates thereof are disclosed; together with processes for their preparation, compositions containing them and their use in therapy. The compounds of formulae (I) and (Ia) are inhibitors of the enzyme nitric oxide synthase and are thereby particularly useful in the treatment or prophylaxis of inflammatory disease.

  公开了使用式（I）的化合物，其中R1、R2、X、Y、V、W和Z如规范中定义，并且其药学上可接受的盐、对映体或消旋体，在制备药物时用于治疗或预防抑制一氧化氮合酶活性有益的疾病或症状。公开了式（Ia）的某些新化合物及其药学上可接受的盐，以及其对映体和消旋体；以及它们的制备方法、含有它们的组合物以及它们在治疗中的应用。式（I）和（Ia）的化合物是一氧化氮合酶酶的抑制剂，因此在治疗或预防炎症性疾病方面特别有用。
• Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
  申请人：——

  公开号：US20030207868A1

  公开（公告）日：2003-11-06

  The present invention concerns antiviral compounds, their methods of preparation and their compositions, and use in the treatment of viral infections. More particularly, the invention provides heterocyclic substituted 2-methylbenzimidazole derivatives for the treatment of respiratory syncytial virus infection.

  本发明涉及抗病毒化合物，其制备方法及其组合物，以及在治疗病毒感染中的应用。更具体地，该发明提供了用于治疗呼吸道合胞病毒感染的杂环取代2-甲基苯并咪唑衍生物。
• NOVEL USE OF PHENYLHETEROALKYLAMINE DERIVATIVES
  申请人：AstraZeneca AB

  公开号：EP1263711A1

  公开（公告）日：2002-12-11
• SUBSTITUTED 2-METHYL-BENZIMIDAZOLE RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1461035A2

  公开（公告）日：2004-09-29
• EP1461035A4
  申请人：——

  公开号：EP1461035A4

  公开（公告）日：2005-04-06