2,3-di(benzoyloxymethyl)furan | 304642-36-2

• 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: 2,3-di(benzoyloxymethyl)furan
• 英文别名: [2-(Benzoyloxymethyl)furan-3-yl]methyl benzoate；[2-(benzoyloxymethyl)furan-3-yl]methyl benzoate
• CAS: 304642-36-2
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: HVAYRJJNYCKIMU-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  464.6±35.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di(benzoyloxymethyl)furan 在 Rh/Al₂O₃ 氢气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 284.0h， 生成 1,6-dibenzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  Structure-Based Design of a Highly Selective Catalytic Site-Directed Inhibitor of Ser/Thr Protein Phosphatase 2B (Calcineurin)

  摘要：

  Protein serine/threonine phosphatases (PP1, PP2A and PP2B) play important roles in intracellular signal transcluctions. The immunosuppressant drugs FK506 and cyclosporin A (CsA) bind to immunophilins, and these complexes selectively inhibit PP2B (calcineurin), leading to the suppression of T-cell proliferation. Both FK506 and CsA must, however, form complexes with immunophilins to exert their inhibitory action on PP2B. Thus, it is of interest to find a direct and selective inhibitor of PP2B that does not involve the immunophilins as a biological tool for studies of PP2B and also as a candidate therapeutic agent. We selected the simple natural product cantharidin, a known PP2A-selective inhibitor, as a lead compound for this project. Primary SAR indicated that norcantharidin (7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride) inhibits not only PP1 and PP2A but also PP2B, and a binding model of norcantharidin carboxylate to the PP2B catalytic site was computationally constructed. Based on this binding model, we designed and synthesized several cantharidin derivatives. Among these compounds, 1, 5-dibenzoyloxymethyl-substituted norcantharidin was found to inhibit PP2B without inhibiting PP1 or PP2A. To our knowledge, this is the first highly selective catalytic site-directed inhibitor of PP2B.

  DOI：

  10.1021/ja034694y
• 作为产物：
  描述：

  3-呋喃甲醇 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,3-di(benzoyloxymethyl)furan
  参考文献：
  名称：

  Structure-Based Design of a Highly Selective Catalytic Site-Directed Inhibitor of Ser/Thr Protein Phosphatase 2B (Calcineurin)

  摘要：

  Protein serine/threonine phosphatases (PP1, PP2A and PP2B) play important roles in intracellular signal transcluctions. The immunosuppressant drugs FK506 and cyclosporin A (CsA) bind to immunophilins, and these complexes selectively inhibit PP2B (calcineurin), leading to the suppression of T-cell proliferation. Both FK506 and CsA must, however, form complexes with immunophilins to exert their inhibitory action on PP2B. Thus, it is of interest to find a direct and selective inhibitor of PP2B that does not involve the immunophilins as a biological tool for studies of PP2B and also as a candidate therapeutic agent. We selected the simple natural product cantharidin, a known PP2A-selective inhibitor, as a lead compound for this project. Primary SAR indicated that norcantharidin (7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride) inhibits not only PP1 and PP2A but also PP2B, and a binding model of norcantharidin carboxylate to the PP2B catalytic site was computationally constructed. Based on this binding model, we designed and synthesized several cantharidin derivatives. Among these compounds, 1, 5-dibenzoyloxymethyl-substituted norcantharidin was found to inhibit PP2B without inhibiting PP1 or PP2A. To our knowledge, this is the first highly selective catalytic site-directed inhibitor of PP2B.

  DOI：

  10.1021/ja034694y

文献信息

• [EN] NUCLEOTIDE ANALOGUES WITH QUATERNARY CARBON STEREOGENIC CENTERS AND METHODS OF USE<br/>[FR] ANALOGUES DE NUCLÉOTIDES COMPORTANT DES CENTRES STÉRÉOGÈNES DE CARBONES QUATERNAIRES ET PROCÉDÉS D'UTILISATION
  申请人：INST RECH S CLINIQUES DE MONTR

  公开号：WO2009115927A2

  公开（公告）日：2009-09-24

  The present invention comprises compounds useful as antiviral or antitumor agents. The compounds comprise nucleotide analogues that comprise tetrahydrofuranyl or tetrahydrothienyl moeities with quaternary centers at the 3' position. The nucleotide analogues can be used to inhibit cancer or viruses. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting diseases or conditions associated with cancers and viruses. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit viruses or tumors and treat, prevent, or inhibit the foregoing diseases.