(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (3R,4S)-4-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-2-oxo-tetrahydro-furan-3-yl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (3R,4S)-4-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-2-oxo-tetrahydro-furan-3-yl ester
• 英文别名: [(3S,4R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-oxo-tetrahydrofuran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate；[(3S,4R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-oxooxolan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₂H₁₈O₁₀
• 分子量: 442.379
• InChiKey: HRPSHJCISIMFNV-LVWDJMLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (3R,4S)-3,4-bis(3,4-diacetoxyphenyl-acryloyloxy)-dihydrofuran-2-one 在 盐酸 作用下， 以 丙酮 为溶剂， 以44%的产率得到(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (3R,4S)-4-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Dicaffeoyl- or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. Such integration is essential for the production of progeny viruses, and therefore therapeutic agents that can inhibit this process should be effective anti-HIV agents. We have previously reported the inhibitory activity of dicaffeoylglucosides against HIV IN. In the present study, we have synthesized and tested dicaffeoyl or digalloyl compounds joined through a five-membered heterocyclic ring as HIV IN inhibitors to explore the SARs of this family of compounds. The starting heterocyclic diols were prepared from L-tartaric acid, diethyl L-tartarate or D-(+)-ribonic gamma -lactone. We found that the HIV IN inhibitory activities of dicaffeoyl derivatives were comparable to that of L-chicoric acid (IC50 = 24.9 muM). On the other hand, digalloyl derivatives were more potent than L-chicoric acid with IC50 Values of 4.7-15.6 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00013-x