6-{1-[(5-hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-{1-[(5-hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione
• 英文别名: 6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione；6-[1-(5-hydroxypentoxy)-2,2-dimethylbut-3-enyl]-5,8-dimethoxynaphthalene-1,4-dione
• 化学式: C₂₃H₃₀O₆
• 分子量: 402.488
• InChiKey: BKYPGXSBNDQOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-{1-[(5-hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以93.5%的产率得到(1E,4E)-6-{1-[(5-hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

  摘要：

  A series of hydroxylated 1,4-naphthoquinone oximes were designed and synthesized. The in vitro cytotoxicity of these compounds was evaluated against five human cancer cell lines and human skin fibroblast cell line. Among them, compounds (1E,4E)-6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8- dimethoxynaphthalene-1,4-dione dioxime and (1E,4E)-6-{1-[(6-Hydroxyhexyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime displayed higher cytotoxicity in three cancer cell lines than the positive drug 5-fluorouracil

  DOI：

  10.1134/s1070363218110221
• 作为产物：
  描述：

  2,2-dimethyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)but-3-en-1-ol 在 盐酸 、 ammonium cerium (IV) nitrate 、 sodium hydride 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 6-{1-[(5-hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 1,4-Naphthoquinone Oxime Derivatives

  摘要：

  A series of hydroxylated 1,4-naphthoquinone oximes were designed and synthesized. The in vitro cytotoxicity of these compounds was evaluated against five human cancer cell lines and human skin fibroblast cell line. Among them, compounds (1E,4E)-6-{1-[(5-Hydroxypentyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8- dimethoxynaphthalene-1,4-dione dioxime and (1E,4E)-6-{1-[(6-Hydroxyhexyl)oxy]-2,2-dimethylbut-3-en-1-yl}-5,8-dimethoxynaphthalene-1,4-dione dioxime displayed higher cytotoxicity in three cancer cell lines than the positive drug 5-fluorouracil

  DOI：

  10.1134/s1070363218110221

文献信息

• Discovery of Dimethyl Shikonin Oxime 5a, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Type 2 Diabetes Mellitus
  作者：Lehao Wu、Jiahua Cui、Chunxiao Zhao、Zeyuan Wang、Jihong Lu、Shaoshun Li、Jinping Jia、Hua Xiao、Yan Zhang

  DOI：10.1021/acs.jmedchem.3c00323

  日期：2023.6.22