(S)-2-(4-{3-[1-(3-Methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoylamino)-succinic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(4-{3-[1-(3-Methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoylamino)-succinic acid
• 英文别名: (2S)-2-[[4-[[3-[(1-isopentylbenzimidazol-2-yl)methyl]-2-oxo-benzimidazol-1-yl]methyl]benzoyl]amino]butanedioic acid；(2S)-2-[[4-[[3-[[1-(3-methylbutyl)benzimidazol-2-yl]methyl]-2-oxobenzimidazol-1-yl]methyl]benzoyl]amino]butanedioic acid
• 化学式: C₃₂H₃₃N₅O₆
• 分子量: 583.644
• InChiKey: CWDBBPSVVKPGIM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-{3-[1-(3-Methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoic acid 在 水 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-(4-{3-[1-(3-Methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzoylamino)-succinic acid
  参考文献：
  名称：

  Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo

  摘要：

  The introduction of acidic and basic functionality into the side chains of respiratory syncytial virus (RSV) fusion inhibitors was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. The acidic compounds 2r, 2u, 2v, 2w, 2z, and 2aj demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the oxadiazolone 2aj reduced virus titers following subcutaneous dosing, whilst the ester 2az and amide 2aab exhibited efficacy following oral administration. These results established the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.109