1-isopentyl-2-((3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid | 950668-53-8

• 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-isopentyl-2-((3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid
• CAS: 950668-53-8
• 化学式: C₂₄H₂₈N₄O₃
• 分子量: 420.511
• InChiKey: UOTHWOUPGSACRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.05
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-isopentyl-2-((3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-[[7-(Hydroxymethyl)-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：

  2-(isopentylamino)-3-nitrobenzonitrile 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 1-isopentyl-2-((3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d]imidazole-7-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