2-butoxy-5,8-dihydroxynaphthalene-1,4-dione | 1599483-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-butoxy-5,8-dihydroxynaphthalene-1,4-dione
• 英文别名: 2-Butoxy-5,8-dihydroxynaphthalene-1,4-dione
• CAS: 1599483-53-0
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: GSZAXPBLKLBCJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5,8-trihydroxy-1,4-naphthoquinone 、 正丁醇 在 硫酸 作用下， 以 水 为溶剂， 反应 12.0h， 以83%的产率得到2-butoxy-5,8-dihydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  醇对酸取代2-羟基-1,4-萘醌的2-O-烷基化反应：多功能合成Spinochrome D及其6-烷氧基衍生物的合成

  摘要：

  摘要 通过将取代的2-羟基-1,4-萘醌与丙-1-醇，丁-1-醇或戊丹-1-酸催化缩合，可获得一系列取代的2-烷氧基-1,4-萘醌衍生物。醇收率高。基于该反应，开发了多用途合成的多色染料D。 通过将取代的2-羟基-1,4-萘醌与丙-1-醇，丁-1-醇或戊丹-1-酸催化缩合，可获得一系列取代的2-烷氧基-1,4-萘醌衍生物。醇收率高。基于该反应，开发了多用途合成的多色染料D。

  DOI：

  10.1055/s-0037-1610415

文献信息

• Chemistry of naphthazarin derivatives. Transetherification selectivity of naphthazarin methoxy derivatives
  作者：N. D. Pokhilo、V. A. Denisenko、V. F. Anufriev

  DOI：10.1134/s1070428014050054

  日期：2014.5

  Transetherification of naphthazarin methoxy derivatives in basic conditions occurs only with primary monohydric alcohols. 1,3-Butanediol due to the assistance of the hydroxy group at the C1 atom gives rise to a mixture of transetherification products at the primary and secondary hydroxy groups in a ratio 3: 1. The reaction with methyl α-D-glucopyranoside affords predominantly methyl 6-O-(5,8-dihydroxy-1

  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。
• 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.