(2S,4aR,8R,8aR)-4,7-dimethyl-2-(2,3,4-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S,4aR,8R,8aR)-4,7-dimethyl-2-(2,3,4-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol
• 英文别名: (2S,4aR,8R,8aR)-4,7-dimethyl-2-(2,3,4-trimethoxyphenyl)-2,3,4a,5,8,8a-hexahydrochromene-4,8-diol
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: YIOSTDZDYFFVHN-YNQOBSGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  马鞭草烯醇 在 montmorillonite K₁₀ Clay 、 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,4aR,8R,8aR)-4,7-dimethyl-2-(2,3,4-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol
  参考文献：
  名称：

  Anti-influenza activity of monoterpene-derived substituted hexahydro-2 H -chromenes

  摘要：

  The antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene (-)-verbenone, was studied for the first time. Five of 11 (45 per cent) of 4-hydroxy-hexahydro-2H-chromene-type compounds have been found to exhibit antiviral activity against influenza A virus of subtype H1N1pdm09. Although a portion of active compounds among 4-fluorine-containing series was fewer, just compound 5i that contains a fluorine substituent exhibited more potent anti-influenza activity along with low cytotoxicity. Thus two new promising types of antiviral compounds were identified. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.037

文献信息

• Synthesis and cytotoxic activity of substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-ones obtained from (–)-verbenone
  作者：I. V. Il’ina、M. A. Pokrovsky、O. S. Mikhalchenko、D. V. Korchagina、K. P. Volcho、A. G. Pokrovsky、N. F. Salakhutdinov

  DOI：10.1007/s11172-015-1148-3

  日期：2015.9

  A number of compounds with a substituted hexahydro-2H-4,6-(epoxymethano)chromen8(5H)-one framework was synthesized starting from monoterpenoid (–)-verbenone and aromatic aldehydes containing methoxy and hydroxy groups. Cytotoxic activity of these compounds on human tumor cell lines was studied for the first time. Compounds containing three methoxy groups in each aromatic ring were found to be the most promising for further studies.

  以单萜(-)-马鞭草烯酮和含有甲氧基和羟基的芳香醛为起始原料，合成了一系列具有取代的六氢-2H-4,6-(环氧亚甲基)色满-8(5H)-酮骨架的化合物。首次研究了这些化合物对人肿瘤细胞系的细胞毒活性。发现每个芳香环中含有三个甲氧基的化合物最具进一步研究的潜力。
• Anti-influenza activity of monoterpene-derived substituted hexahydro-2 H -chromenes
  作者：Oksana S. Patrusheva、Vladimir V. Zarubaev、Anna A. Shtro、Yana R. Orshanskaya、Sergey A. Boldyrev、Irina V. Ilyina、Svetlana Yu. Kurbakova、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmc.2016.08.037

  日期：2016.11

  The antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene (-)-verbenone, was studied for the first time. Five of 11 (45 per cent) of 4-hydroxy-hexahydro-2H-chromene-type compounds have been found to exhibit antiviral activity against influenza A virus of subtype H1N1pdm09. Although a portion of active compounds among 4-fluorine-containing series was fewer, just compound 5i that contains a fluorine substituent exhibited more potent anti-influenza activity along with low cytotoxicity. Thus two new promising types of antiviral compounds were identified. (C) 2016 Elsevier Ltd. All rights reserved.