3-(3-hydroxy-3-methylbutyl)-6-methoxy-2,4-dimethoxymethylacetophenone | 1044743-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-hydroxy-3-methylbutyl)-6-methoxy-2,4-dimethoxymethylacetophenone
• 英文别名: 1-[3-(3-Hydroxy-3-methylbutyl)-6-methoxy-2,4-bis(methoxymethoxy)phenyl]ethanone
• CAS: 1044743-44-3
• 化学式: C₁₈H₂₈O₇
• 分子量: 356.416
• InChiKey: BLDSBFFLZBKILZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-3-methylbutyl)-6-methoxy-2,4-dimethoxymethylacetophenone 、 1-[3-甲氧基-4-(甲氧基甲氧基)苯基]乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.01.060
• 作为产物：
  描述：

  1-[6-methoxy-2,4-dimethoxymethyloxy-3-(3-methyl-but-2-enyl)-phenyl]-ethanone 在 sodium hydroxide 、 mercury(II) diacetate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以70%的产率得到3-(3-hydroxy-3-methylbutyl)-6-methoxy-2,4-dimethoxymethylacetophenone
  参考文献：
  名称：

  Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from Humulus lupulus

  摘要：

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

  DOI：

  10.1021/np800188b