2,3,5,6-tetramethoxy-phenanthrene-9-carboxylic acid | 35676-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3,5,6-tetramethoxy-phenanthrene-9-carboxylic acid
• 英文别名: 2,3,5,6-Tetramethoxy-9-carboxy-phenanthren；2,3,5,6-Tetramethoxy-phenanthrencarbonsaeure-(9)；2,3,5,6-Tetramethoxy-phenanthren-9-carbonsaeure
• CAS: 35676-01-8
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: RAHVGVMSRMVGHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetramethoxy-phenanthrene-9-carboxylic acid 在 喹啉 、 copper(II) sulfate 作用下， 生成 2,3,5,6-tetramethoxyphenanthrene
  参考文献：
  名称：

  Tylophora哮喘的化学检查-II

  摘要：

  酪氨酸已降解为2：3：6：7-四甲氧基-9-甲基菲化合物。结合其他降解结果和生物遗传因素，现在将酪氨酸定为2：3：6：7-四甲氧基菲（9：10：6'：7'）吲哚并立定。

  DOI：

  10.1016/0040-4020(58)80052-6
• 作为产物：
  描述：

  2,3,5,6-Tetramethoxy-phenanthrencarbonsaeure-(9)-methylester 在 甲醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2,3,5,6-tetramethoxy-phenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

  摘要：

  Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.05.074

文献信息

• 189. The alkaloids of Tylophora crebriflora: structure and synthesis of tylocrebrine, a new phenanthroindolizidine alkaloid
  作者：E. Gellert、T. R. Govindachari、M. V. Lakshmikantham、I. S. Ragade、R. Rudzats、N. Viswanathan

  DOI：10.1039/jr9620001008

  日期：——