2-[3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazol-5-yl]acetonitrile | 554457-63-5

• 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: 2-[3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazol-5-yl]acetonitrile
• CAS: 554457-63-5
• 化学式: C₂₅H₂₉N₅O
• 分子量: 415.538
• InChiKey: GMZRKFGYXNNTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazol-5-yl]acetonitrile 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 1-[[6-(2-Aminoethyl)-1-(3-methylbutyl)benzimidazol-2-yl]methyl]-3-propan-2-ylbenzimidazol-2-one
  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 、 lithium aluminium tetrahydride 、 氯化亚砜 、 TEA 、 硫酸 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-[3-(3-Methylbutyl)-2-[(2-oxo-3-propan-2-ylbenzimidazol-1-yl)methyl]benzimidazol-5-yl]acetonitrile
  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

• 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。
• Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity
  作者：Xiangdong Alan Wang、Christopher W. Cianci、Kuo-Long Yu、Keith D. Combrink、Jan W. Thuring、Yi Zhang、Rita L. Civiello、Kathleen F. Kadow、Julia Roach、Zhufang Li、David R. Langley、Mark Krystal、Nicholas A. Meanwell

  DOI：10.1016/j.bmcl.2007.05.102

  日期：2007.8

  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.