meso-1,4-bis-(2-bromo-4,5-dimethoxy-phenyl)-2,3-dimethyl-butane | 36287-35-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: meso-1,4-bis-(2-bromo-4,5-dimethoxy-phenyl)-2,3-dimethyl-butane
• 英文别名: meso-1,4-Bis-(2-brom-4,5-dimethoxy-phenyl)-2,3-dimethyl-butan；Inaktives β.γ-Dimethyl-α.δ-bis-(6-brom-3.4-dimethoxy-phenyl)-butan；meso-1,4-Bis-(2-brom-4,5-dimethoxyphenyl)-2,3-dimethylbutan；1-bromo-2-[(2S,3R)-4-(2-bromo-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-4,5-dimethoxybenzene
• CAS: 36287-35-1
• 化学式: C₂₂H₂₈Br₂O₄
• 分子量: 516.27
• InChiKey: NRGPUQUPAQXDJI-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-1,4-bis-(2-bromo-4,5-dimethoxy-phenyl)-2,3-dimethyl-butane 在 三溴化硼 作用下， 生成 4-bromo-5-[(2R,3S)-4-(2-bromo-4,5-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Nordihydroguaiaretic Acid Inhibitors toward Soybean, 12-Human, and 15-Human Lipoxygenase

  摘要：

  Lipoxygenase (LO) is a biological target for many diseases such as asthma, atherosclerosis, and cancer. Our labs have synthesized and investigated nordihydroguaiaretic acid (NDGA) derivatives and have established that the reductive inhibition of soybean and 15-human LO can be affected by the strength of the electron-withdrawing substituents on the phenyl rings of NDGA. In addition, we have determined that hydrophobic NDGA derivatives activate 15-HLO, suggesting a hydrophobic allosteric site.

  DOI：

  10.1021/jm0201262
• 作为产物：
  描述：

  1,1'-(2,3-二甲基-1,4-丁烷二基)二(3,4-二甲氧基苯) 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 meso-1,4-bis-(2-bromo-4,5-dimethoxy-phenyl)-2,3-dimethyl-butane
  参考文献：
  名称：

  Synthesis of Lignans. I. Nordihydroguaiaretc Acid

  摘要：

  DOI：

  10.1021/jo00799a605

文献信息

• Schroeter; Lichtenstadt; Irineu, Chemische Berichte, 1918, vol. 51, p. 1600
  作者：Schroeter、Lichtenstadt、Irineu

  DOI：——

  日期：——
• Synthesis of Lignans. I. Nordihydroguaiaretc Acid
  作者：Clark W. Perry、Malda V. Kalnins、Kenneth H. Deitcher

  DOI：10.1021/jo00799a605

  日期：1972.7.29
• Structure−Activity Relationship Studies of Nordihydroguaiaretic Acid Inhibitors toward Soybean, 12-Human, and 15-Human Lipoxygenase
  作者：Stephanie Whitman、Mikail Gezginci、Barbara N. Timmermann、Theodore R. Holman

  DOI：10.1021/jm0201262

  日期：2002.6.1

  Lipoxygenase (LO) is a biological target for many diseases such as asthma, atherosclerosis, and cancer. Our labs have synthesized and investigated nordihydroguaiaretic acid (NDGA) derivatives and have established that the reductive inhibition of soybean and 15-human LO can be affected by the strength of the electron-withdrawing substituents on the phenyl rings of NDGA. In addition, we have determined that hydrophobic NDGA derivatives activate 15-HLO, suggesting a hydrophobic allosteric site.