5,8-dihydroxy-2-(3-hydroxybutoxy)naphthalene-1,4-dione | 1599483-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2-(3-hydroxybutoxy)naphthalene-1,4-dione
• 英文别名: 2-(3-hydroxybutoxy)naphthazarin
• CAS: 1599483-55-2
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: DYQUGGVNLSUFLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104.06
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,3-丁二醇 、 5,8-二羟基-2-甲氧基-1,4-萘醌 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 4.0h， 以60%的产率得到5,8-dihydroxy-2-(3-hydroxybutoxy)naphthalene-1,4-dione
  参考文献：
  名称：

  萘他林衍生物的化学。萘他林甲氧基衍生物的醚交换选择性

  摘要：

  在基本条件下萘萘甲氧基衍生物的醚交换作用仅与伯一元醇发生。1,3-丁二醇由于在C 1原子上的羟基的辅助作用，在伯羟基和仲羟基上以3：1的比例生成了醚交换产物的混合物。与甲基α-D-吡喃葡萄糖苷反应得到主要是甲基6 - O-（5,8-二羟基-1,4-二氧杂萘-2-基）-α-D-吡喃葡萄糖苷，以前未知的水溶性萘醌-碳水化合物共轭物。

  DOI：

  10.1134/s1070428014050054

文献信息

• Quinone–carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: Synthesis and determination of in vitro activity
  作者：Dmitry N. Pelageev、Sergey A. Dyshlovoy、Nataly D. Pokhilo、Vladimir A. Denisenko、Ksenia L. Borisova、Gunhild Keller-von Amsberg、Carsten Bokemeyer、Sergey N. Fedorov、Friedemann Honecker、Victor Ph. Anufriev

  DOI：10.1016/j.ejmech.2014.03.006

  日期：2014.4

  We have found that 2-methoxy-1,4-naphthoquinones easily react with primary alcohols to produce the corresponding 2-alkoxyderivatives. Using this reaction, we synthesized methyl-6-O-(naphthalene-1,4-dione-2-yl)-alpha-D-glucopyranosides, a new type of water soluble quinone-carbohydrate nonglucoside conjugates. The resulting conjugates induced apoptosis in human cancer HeLa and normal mouse JB6 P+ Cl41 cells with simultaneous inhibition of p53-dependant transcriptional activity, suggesting that the observed cell death was p53-independent. Furthermore, we analyzed structure-activity relationship and bioactivity of 2-hydroxy- and 2-methoxy-1,4-naphthoquinones as well as carbohydrate nonglucoside conjugates. All compounds containing a quinone moiety were able to inhibit p53-dependant transcriptional activity and exerted moderate inhibitory effects on HeLa cell colony formation. Investigations of structure-activity relationships revealed that cytotoxicity depended on the type of substituent at C-2 of the quinone moiety, decreasing in the following order: methoxyderivatives > carbohydrate nonglucoside conjugates > hydroxyderivatives. Furthermore, cytotoxicity depended on the position of the hydroxy substituent in the quinone moiety in all derivatives and decreased in the following order: 8- 5- > 5,8-derivatives.In conclusion, this is the first report on synthesis and biological structure-activity relationships of the new class of quinone-carbohydrate nonglucoside conjugates. (c) 2014 Elsevier Masson SAS. All rights reserved.