2,2',4,4',6'-pentamethoxychalcone | 25163-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,2',4,4',6'-pentamethoxychalcone
• 英文别名: 2,4,2',4',6'-pentamethoxy-chalcone；2,4,2',4',6'-Pentamethoxy-chalkon；2.4.2'.4'.6'-Pentamethoxy-chalkon；3-(2,4-Dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 25163-69-3
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: BGOHJRNMDGOPSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 2,2',4,4',6'-pentamethoxychalcone 在 thallium(III) nitrate 作用下， 生成 2-(2,4-Dimethoxyphenyl)-3,3-dimethoxy-1-(2,4,6-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  Horie, Tokunaru; Kawamura, Yasuhiko; Sakai, Chikako, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 753 - 760

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三甲氧基苯乙酮 、 2,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以67%的产率得到2,2',4,4',6'-pentamethoxychalcone
  参考文献：
  名称：

  Investigation of Chalcones as Selective Inhibitors of the Breast Cancer Resistance Protein: Critical Role of Methoxylation in both Inhibition Potency and Cytotoxicity

  摘要：

  ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 mu M and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6'-hydroxyl-2',4'-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.

  DOI：

  10.1021/jm2016528

文献信息

• Kauffmann; Kieser, Chemische Berichte, 1913, vol. 46, p. 3799
  作者：Kauffmann、Kieser

  DOI：——

  日期：——
• Investigation of Chalcones as Selective Inhibitors of the Breast Cancer Resistance Protein: Critical Role of Methoxylation in both Inhibition Potency and Cytotoxicity
  作者：Glaucio Valdameri、Charlotte Gauthier、Raphaël Terreux、Rémy Kachadourian、Brian J. Day、Sheila M. B. Winnischofer、Maria E. M. Rocha、Véronique Frachet、Xavier Ronot、Attilio Di Pietro、Ahcène Boumendjel

  DOI：10.1021/jm2016528

  日期：2012.4.12

  ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 mu M and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6'-hydroxyl-2',4'-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.
• Horie, Tokunaru; Kawamura, Yasuhiko; Sakai, Chikako, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 753 - 760
  作者：Horie, Tokunaru、Kawamura, Yasuhiko、Sakai, Chikako、Akita, Ayako、Kuramoto, Masafumi

  DOI：——

  日期：——