5-Hydroxy-6-methoxycarbonyl-4-oxo-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-Hydroxy-6-methoxycarbonyl-4-oxo-pyran-2-carboxylic acid
• 英文别名: 5-hydroxy-6-methoxycarbonyl-4-oxopyran-2-carboxylic acid
• 化学式: C₈H₆O₇
• 分子量: 214.131
• InChiKey: UTGAHNRTEAZJDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  罌粟酸 在 sodium hydroxide 、 乙酰氯 作用下， 反应 96.75h， 生成 5-Hydroxy-6-methoxycarbonyl-4-oxo-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

文献信息

• The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase
  作者：Paola Pace、Emanuela Nizi、Barbara Pacini、Silvia Pesci、Victor Matassa、Raffaele De Francesco、Sergio Altamura、Vincenzo Summa

  DOI：10.1016/j.bmcl.2004.03.087

  日期：2004.6

  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.