2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trimethoxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one | 50991-85-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trimethoxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 英文别名: 2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3-[O²,O³,O⁴-trimethyl-O⁶-(tri-O-methyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chromen-4-one；2-(3,4-Dimethoxy-phenyl)-5,7-dimethoxy-3-[O²,O³,O⁴-trimethyl-O⁶-(tri-O-methyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chromen-4-on；2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 50991-85-0
• 化学式: C₃₇H₅₀O₁₆
• 分子量: 750.794
• InChiKey: DUEWOIURGPXKOB-IDHYXCNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  芦丁 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以44.2%的产率得到2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trimethoxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells

  摘要：

  Three methylated quercetins and a series of O-3 substituted 5,7,3',4'-tetra-O-methylated quercetin derivatives have been synthesized and evaluated on the modulating activity of P-gp, BCRP and MRP1 in cancer cell lines. Compound 17 (with a 2-((4-methoxybenzoyl)oxy)ethyl at O-3) is the most potent P-gp modulator. Three derivatives, compound 9 (3,7,3',4'-tetra-O-methylated quercetin), compound 14 (with a 2-((3-oxo-3-(3,4,5trimethoxyphenyl)prop-1-en-1-yl)oxy)ethyl at O-3) and compound 17, consistently exhibited promising BCRP-modulating activity. Interestingly, compound 17 was found to be equipotent against both P-gp and BCRP Importantly, these synthetic quercetin derivatives did not exhibit any inherent cytotoxicity to cancer cell lines or normal mouse fibroblast cell lines. These quercetin derivatives can be employed as safe and effective modulators of P-gp- or BCRP-mediated drug resistance in cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.026

文献信息

• Zemplen; Tettamanti, Chemische Berichte, 1938, vol. 71, p. 2511,2512, 2515
  作者：Zemplen、Tettamanti

  DOI：——

  日期：——
• Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells
  作者：Jian Yuan、Iris L.K. Wong、Tao Jiang、Si Wen Wang、Tao Liu、Bin Jin Wen、Larry M.C. Chow、Biao Wan Sheng

  DOI：10.1016/j.ejmech.2012.05.026

  日期：2012.8

  Three methylated quercetins and a series of O-3 substituted 5,7,3',4'-tetra-O-methylated quercetin derivatives have been synthesized and evaluated on the modulating activity of P-gp, BCRP and MRP1 in cancer cell lines. Compound 17 (with a 2-((4-methoxybenzoyl)oxy)ethyl at O-3) is the most potent P-gp modulator. Three derivatives, compound 9 (3,7,3',4'-tetra-O-methylated quercetin), compound 14 (with a 2-((3-oxo-3-(3,4,5trimethoxyphenyl)prop-1-en-1-yl)oxy)ethyl at O-3) and compound 17, consistently exhibited promising BCRP-modulating activity. Interestingly, compound 17 was found to be equipotent against both P-gp and BCRP Importantly, these synthetic quercetin derivatives did not exhibit any inherent cytotoxicity to cancer cell lines or normal mouse fibroblast cell lines. These quercetin derivatives can be employed as safe and effective modulators of P-gp- or BCRP-mediated drug resistance in cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.