3-furylmethyl benzoate | 98096-44-7

• 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: 3-furylmethyl benzoate
• 英文别名: (furan-3-yl)methyl benzoate；Furan-3-ylmethyl benzoate
• CAS: 98096-44-7
• 化学式: C₁₂H₁₀O₃
• mdl: MFCD00075047
• 分子量: 202.21
• InChiKey: NHIRTJIIALGHKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-furylmethyl benzoate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  3-呋喃甲醇 、 苯甲酰氯 在 吡啶 作用下， 反应 3.0h， 以97%的产率得到3-furylmethyl benzoate
  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

• Copper‐mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols
  作者：Jianyu Dong、Xiuling Chen、Fangyan Ji、Lixin Liu、Lebin Su、Min Mo、Jian‐Sheng Tang、Yongbo Zhou

  DOI：10.1002/aoc.6073

  日期：2021.1

  A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of CH bond, cleavage of inert CC bond, and formation of CO

  在铜盐和分子氧的存在下，芳基乙腈与醇/酚的简单直接的好氧氧化酯化反应得以实现，从而以良好或高收率生产了多种芳基羧酸酯。铜盐起着变换，这允许C的氧合多个角色 H键的，惰性的C裂解 C键，C和形成一锅O键而没有任何的酸，碱，配体的帮助下，等等。该反应提供了从容易获得的起始原料向官能化的酯，特别是苯甲酸芳基酯的简单，直接和有效的方案。
• 一种杂环酯类化合物的制备方法
  申请人：河南农业大学

  公开号：CN113979955A

  公开（公告）日：2022-01-28

  本发明公开了一种杂环酯类化合物的制备方法，包括下列步骤：将羟甲基取代杂环化合物、苯甲酰腈衍生物加入有机溶剂中进行搅拌反应24h，然后冷却至室温，得到反应液；将所得反应液进行浓缩，分离纯化，即得。本发明实现了在无金属和无氧化剂条件下制备杂环酯类化合物的简便有效方法，以经济易得的羟甲基取代杂环化合物和苯甲酰腈衍生物为原料，直接在溶剂中搅拌发生C‑C键断裂，经过酰化反应生成相应的杂环酯类化合物，该类化合物可用于香料、药物和有机合成等领域。本发明合成体系适用范围较广，兼容烷基、烷氧基、各种卤素原子等官能团，不需要惰性气体保护条件，反应条件温和，底物范围较广，具有较高的产率。
• Structure-based design of novel calcineurin (PP2B) inhibitors
  作者：John H. Tatlock、M. Angelica Linton、Xinjun J. Hou、Charles R. Kissinger、Laura A. Pelletier、Richard E. Showalter、Anna Tempczyk、J. Ernest Villafranca

  DOI：10.1016/s0960-894x(97)00141-8

  日期：1997.4

  The design, synthesis, and evaluation of small molecule, in vitro, inhibitors of human calcineurin is described. These ligands were derived from the known nonspecific phosphatase inhibitor endothall, and were modified to enhance binding and selectivity toward calcineurin using protein crystal structure information. (C) 1997 Elsevier Science Ltd.
• Structure-activity relationship of cantharidin derivatives to protein phosphatases 1, 2A1, and 2B
  作者：Mikiko Sodeoka、Yoshiyasu Baba、Satoko Kobayashi、Nozomu Hirukawa

  DOI：10.1016/s0960-894x(97)00316-8

  日期：1997.7

  The effects of structural modification of cantharidin on the inhibition of protein Ser/Thr phosphatases are described. Removal of the methyl substituents at C2 and C3 in cantharidin improved the inhibition of PP2B. In contrast, introduction of a substituent to C1/C4-position drastically decreased inhibition of PP1 and PP2A(1). PP2B was found to be quite tolerant to modifications at the C5 position. (C) 1997 Elsevier Science Ltd.
• Jurasek, Adolf; Zvak, Vladimir; Kovac, Jaroslav, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 9, p. 2077 - 2083
  作者：Jurasek, Adolf、Zvak, Vladimir、Kovac, Jaroslav、Rajniakova, Olga、Stetinova, Jarmila

  DOI：——

  日期：——