4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalcone

• 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: 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalcone
• 英文别名: 4-O-acetylxanthohumol；[4-[(E)-3-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-oxoprop-1-enyl]phenyl] acetate
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: SETJXTDZSDYIJJ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  黄腐酚 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以33.1%的产率得到4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalcone
  参考文献：
  名称：

  黄腐酚酚酰基衍生物的抗增殖和抗氧化活性

  摘要：

  合成了一系列单酰基和二酰基黄腐酚（1）衍生物，产率为10％至30％。使用SRB测定法测试了所有化合物对结肠癌细胞（HT-29）的人癌细胞系的抗增殖活性。活性最高的（IC50值<12μM）是三种化合物：4-O-乙酰基黄腐酚（2）（IC50 = 11.84μM ），4,4'-Di-O-乙酰基黄腐酚（3）（IC50 = 11.75μM ）和4 -十一烷酰基黄腐酚（4）（IC50 = 10.04μM ）。对于起始化合物黄腐酚（1）IC50 = 9.74μM。抗氧化剂活性通过2.2-二苯基-1-吡啶并肼基和2，2′-叠氮基-双-3-乙基苯并噻唑啉-6-磺酸的方法测定，并表示为每克Trolox当量抗氧化剂容量。仅一种化合物4-O-乙酰基黄腐酚（2）（15μMTrolox等效抗氧化能力对2,2-二苯基-1-吡啶并肼基和160μMTrolox等效抗氧化能力对2,2'-氮杂-双-3-乙基苯并噻唑啉与黄腐酚相

  DOI：

  10.1007/s00044-017-1887-9

文献信息

• Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect
  作者：Susanne Vogel、Matej Barbic、Guido Jürgenliemk、Jörg Heilmann

  DOI：10.1016/j.ejmech.2010.01.060

  日期：2010.6

  Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were synthesized by combination of the B-Ring fragments of helichrysetin, xanthohumol, xanthohumol C and xanthohumol H with ferulic or caffeic acid moieties in Ring A. Compound 3 showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3 +/- 04 mu M. Anti-oxidative effects were determined in the ORAC assay and revealed very strong activity for 3 and 3-methoxyhelichrysetin (6) exhibiting 7.7 +/- 0.3 and 6.0 +/- 1.3 Trolox equivalents, respectively. The anti-inflammatory activity of all compounds was measured in an in vitro ICAM-1 assay with human microvascular endothelial cells (HMEC-1) and compared with the activity of other structurally related chalcones. The results showed increasing anti-inflammatory activity for the new synthetic chalcones exhibiting a caffeoyl substructure with 3-hydroxyhelichrysetin (5) and 3-hydroxyxanthohumol H (14) being the most active. At 10 mu M the TNF alpha induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, respectively.