3-(3-甲氧基-4-(甲氧基甲氧基)苯基)-1-(2,4,6-三(甲氧基甲氧基)苯基)丙-2-烯-1-酮 | 1334307-40-2

• 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
• 中文名称: 3-(3-甲氧基-4-(甲氧基甲氧基)苯基)-1-(2,4,6-三(甲氧基甲氧基)苯基)丙-2-烯-1-酮
• 英文名称: 3-(3-methoxy-4-(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)prop-2-en-1-one
• CAS: 1334307-40-2
• 化学式: C₂₄H₃₀O₁₀
• 分子量: 478.496
• InChiKey: OMZLHSIUXHRTMO-UHFFFAOYSA-N

物化性质

• 沸点：
  616.0±55.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  34.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-(3-甲氧基-4-(甲氧基甲氧基)苯基)-1-(2,4,6-三(甲氧基甲氧基)苯基)丙-2-烯-1-酮 在 盐酸 、 potassium pyrosulfite 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 9.33h， 生成 异鼠李素
  参考文献：
  名称：

  Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

  摘要：

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.008
• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 、 1-[2,4,6-三(甲氧基甲氧基)苯基]乙酮 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以85%的产率得到3-(3-甲氧基-4-(甲氧基甲氧基)苯基)-1-(2,4,6-三(甲氧基甲氧基)苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

  摘要：

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.008

文献信息

• Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells—A SAR study
  作者：K. Amrutha、Pandurangan Nanjan、Sanu K. Shaji、Damu Sunilkumar、K. Subhalakshmi、Lakshmi Rajakrishna、Asoke Banerji

  DOI：10.1016/j.bmcl.2014.07.093

  日期：2014.10

  Seventeen flavonoids with different substitutions were evaluated for inhibition of nuclear factor-kappa B (NF-kappa B) signaling in the invasive breast cancer cell line MDA-MB-231. They were screened using an engineered MDA-MB-231 cell line reporting NF-kappa B activation. The modulation of expression of two NF-kappa B regulated genes involved in tumorigenesis, matrix metalloproteinase-9 (MMP-9), and cyclooxygenase-2 (COX-2) were also analyzed in these cells. Among the compounds tested, all except gossypetin and quercetagetin inhibited the activation of NF-kappa B, and the expression of MMP-9 and COX-2 to different degree. Methylated flavone, chrysoeriol (luteolin-3'-methylether), was found to be the most potent inhibitor of MMP-9 and COX-2 expressions. The effect of chrysoeriol on cell proliferation, cell cycle, apoptosis and metastasis was analyzed by established methods. Chrysoeriol caused cell cycle arrest at G2/M and inhibited migration and invasion of MDA-MB-231 cells. The structure-activity relations amongst the flavonoids as NF-kappa B signaling inhibitors was studied. The study indicates differences between the actions of various flavonoids on NF-kappa B activation and on the biological activities of breast cancer cells. Flavones in general, were more active than the corresponding flavonols. (C) 2014 Elsevier Ltd. All rights reserved.