6-(4-(3-chloro-4-(methylsulfonyl)phenyl)-2-cyclopentyl-2-hydroxybutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one | 945619-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(4-(3-chloro-4-(methylsulfonyl)phenyl)-2-cyclopentyl-2-hydroxybutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• CAS: 945619-22-7
• 化学式: C₂₂H₂₉ClO₆S
• 分子量: 456.988
• InChiKey: HOQLUNPCSYEQSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-(4-(3-chloro-4-(methylsulfonyl)phenyl)-2-cyclopentyl-2-hydroxybutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 6-{2-[3-chloro-4-(methylsulfonyl)phenyl]ethyl}-6-cyclopentyl-3-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Allosteric Inhibitors of Hepatitis C Polymerase:  Discovery of Potent and Orally Bioavailable Carbon-Linked Dihydropyrones

  摘要：

  The discovery and optimization of a novel class of carbon-linked dihydropyrones as allosteric HCV NS5B polymerase inhibitors are presented. Replacement of the sulfur linker atom with carbon reduced compound acidity and greatly increased cell permeation. Further structure-activity relationship (SAR) studies led to the identification of compounds, exemplified by 23 and 24, with significantly improved antiviral activities in the cell-based replicon assay and favorable pharmacokinetic profiles.

  DOI：

  10.1021/jm0704447
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium dihydroxide 、 copper(l) iodide 氢气 、 二异丙胺 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 6-(4-(3-chloro-4-(methylsulfonyl)phenyl)-2-cyclopentyl-2-hydroxybutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Allosteric Inhibitors of Hepatitis C Polymerase:  Discovery of Potent and Orally Bioavailable Carbon-Linked Dihydropyrones

  摘要：

  The discovery and optimization of a novel class of carbon-linked dihydropyrones as allosteric HCV NS5B polymerase inhibitors are presented. Replacement of the sulfur linker atom with carbon reduced compound acidity and greatly increased cell permeation. Further structure-activity relationship (SAR) studies led to the identification of compounds, exemplified by 23 and 24, with significantly improved antiviral activities in the cell-based replicon assay and favorable pharmacokinetic profiles.

  DOI：

  10.1021/jm0704447