Meconsaeure-diethylester | 729-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Meconsaeure-diethylester
• 英文别名: Mekonsaeure-diethylester；3-hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid diethyl ester；3-Hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid diethyl ester；diethyl 3-hydroxy-4-oxopyran-2,6-dicarboxylate
• CAS: 729-63-5
• 化学式: C₁₁H₁₂O₇
• 分子量: 256.212
• InChiKey: CWZGQDOSIVDCEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  422.3±45.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Meconsaeure-diethylester 、 乙酰氯 生成 3-acetoxy-4-oxo-4H-pyran-2,6-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  [关于γ-吡喃酮的研究。2.关于胎粪酸衍生物的光学性质]。

  摘要：

  DOI：

  10.1002/ardp.19592920707
• 作为产物：
  描述：

  罌粟酸 、 乙醇 在 乙酰氯 作用下， 反应 96.0h， 生成 Meconsaeure-diethylester
  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

• Gorjaew et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2102,2105; engl. Ausg. S. 2140, 2143
  作者：Gorjaew et al.

  DOI：——

  日期：——
• SATO K.; OHASHI M.; AOKI E.; MURAI Y., J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 23, 3713-3716
  作者：SATO K.、 OHASHI M.、 AOKI E.、 MURAI Y.

  DOI：——

  日期：——
• 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.
• Untersuchungen an γ-Pyronen 2. Mitt.: Über optische Eigenschaften von Mekonsäurederivaten
  作者：Fritz Eiden

  DOI：10.1002/ardp.19592920707

  日期：——