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methyl 6-О-(5,8-dihydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside | 1599483-57-4

中文名称
——
中文别名
——
英文名称
methyl 6-О-(5,8-dihydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside
英文别名
methyl 6-O-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-α-D-glucopyranoside;methyl 6-O-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-alpha-d-glucopyranoside;5,8-dihydroxy-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]naphthalene-1,4-dione
methyl 6-О-(5,8-dihydroxynaphthalene-1,4-dione-2-yl)-α-D-glucopyranoside化学式
CAS
1599483-57-4
化学式
C17H18O10
mdl
——
分子量
382.324
InChiKey
CRCUZMYCSZHCEV-AUMBKBSLSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -0.1
  • 重原子数:
    27
  • 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:
    163
  • 氢给体数:
    5
  • 氢受体数:
    10

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    5,8-二羟基-2-甲氧基-1,4-萘醌alpha-甲基葡萄糖甙sodium methylate 作用下, 以 甲醇二甲基亚砜 为溶剂, 反应 3.0h, 以66%的产率得到methyl 6-О-(5,8-dihydroxynaphthalene-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
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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.
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