(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-en-1-one | 1034276-30-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-en-1-one
• CAS: 1034276-30-6
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: SPNYLXUWJCPWKK-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以69%的产率得到(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

  摘要：

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.079

文献信息

• Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
  作者：Susanne Vogel、Susanne Ohmayer、Gabi Brunner、Jörg Heilmann

  DOI：10.1016/j.bmc.2008.02.079

  日期：2008.4

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.