6-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid | 722500-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
• CAS: 722500-66-5
• 化学式: C₂₂H₂₀O₇
• 分子量: 396.397
• InChiKey: LIJQNOFYPKNDOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95.2
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-Benzyloxymethyl-3-hydroxy-4-oxo-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase

  摘要：

  Screening of the in-house sample collection for compounds with HCV NS5B RNA dependent RNA polymerase inhibition led to the identification of a new lead. Afterwards, we discovered that the screening lead, rather than containing the expected structure 1, was comprised of roughly a 1:1 mixture of meconic acid 2 and its monoethyl ester 3, with all inhibitory potency residing with 3. We propose that this compound shares critical common features for activity with alpha,gamma-diketoacids inhibitors previously discovered by our group. SAR around this molecule will be presented to provide an improved basis for structure-based ligand design. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.087
• 作为产物：
  描述：

  2-(benzyloxymethyl)-5-hydroxy-4H-pyran-4-one 在 manganese(IV) oxide 、 sodium hydroxide 、 氰化钠 、 caesium carbonate 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 6-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase

  摘要：

  Screening of the in-house sample collection for compounds with HCV NS5B RNA dependent RNA polymerase inhibition led to the identification of a new lead. Afterwards, we discovered that the screening lead, rather than containing the expected structure 1, was comprised of roughly a 1:1 mixture of meconic acid 2 and its monoethyl ester 3, with all inhibitory potency residing with 3. We propose that this compound shares critical common features for activity with alpha,gamma-diketoacids inhibitors previously discovered by our group. SAR around this molecule will be presented to provide an improved basis for structure-based ligand design. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.087