2-(Ethoxymethyl)-5-phenylmethoxypyran-4-one | 181431-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(Ethoxymethyl)-5-phenylmethoxypyran-4-one
• CAS: 181431-42-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: KHLQVYUSLIUOQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Ethoxymethyl)-5-phenylmethoxypyran-4-one 在 盐酸 、 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 35.0h， 生成 6-(乙氧基甲基)-3-羟基-4-氧代-4H-吡喃-2-羧酸
  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：

  曲酸 在 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(Ethoxymethyl)-5-phenylmethoxypyran-4-one
  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

• Synthesis, Physicochemical Properties, and Biological Evaluation of Hydroxypyranones and Hydroxypyridinones:  Novel Bidentate Ligands for Cell-Labeling
  作者：Beverley L. Ellis、Anne K. Duhme、Robert C. Hider、M. Bilayet Hossain、Safia Rizvi、Dick van der Helm

  DOI：10.1021/jm960220g

  日期：1996.1.1

  The synthesis of a range of hydroxypyranones and hydroxypyridinones with potential for the chelation of indium(III) is described. The crystal structures of two of the indium complexes are presented. The distribution coefficients of the ligands and the corresponding iron(III), gallium(III), and indium(III) complexes are reported. Good linear relationships between the distribution coefficients of the

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。
• 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.