methyl 6-О-(5-hydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside | 1599483-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-О-(5-hydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside
• 英文别名: 5-hydroxy-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]naphthalene-1,4-dione
• CAS: 1599483-58-5
• 化学式: C₁₇H₁₈O₉
• 分子量: 366.325
• InChiKey: FKBLMGDBUJPMMF-UFRBAHOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-methoxy-5-hydroxy-1,4-naphthoquinone 、 alpha-甲基葡萄糖甙 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 3.0h， 以33%的产率得到methyl 6-О-(5-hydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside
  参考文献：
  名称：

  Quinone–carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: Synthesis and determination of in vitro activity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.03.006

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.