6,8-bis(morpholin-4-ylmethyl)genistein | 1351204-09-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6,8-bis(morpholin-4-ylmethyl)genistein
• 英文别名: 5,7-Dihydroxy-3-(4-hydroxyphenyl)-6,8-bis(morpholin-4-ylmethyl)chromen-4-one
• CAS: 1351204-09-5
• 化学式: C₂₅H₂₈N₂O₇
• 分子量: 468.507
• InChiKey: XIFZVTYMVHBENE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 染料木素 以 甲醇 为溶剂， 反应 6.0h， 以49%的产率得到6,8-bis(morpholin-4-ylmethyl)genistein
  参考文献：
  名称：

  Genistein Binding Mode to Doubly Nicked Dumbbell DNA. Dynamic and Diffusion Ordered NMR Study

  摘要：

  New genistein derivatives were synthesized, which are fairly well soluble in water, with respect to parent genistein, and thus facilitate study of the interaction with dumbbell DNA dodecamer, mimicking the biological target for topoisomerase II inhibitors. A pulsed field gradient spin echo NMR experiment was used to check the binding and to estimate the association constants and its pH dependence of genistein with dumbbell DNA. Experimental restraints based on nuclear Overhauser spectroscopy spectra were used to calculate the NMR structure in solution in case of 6,8-disubstituted genistein with dimethylaminomethyl groups and were used in molecular modeling calculations. The structure is dynamic, and 10 molecular dynamics runs yield a family of conformations that essentially differ in a depth of inclusion of genistein into a nick. The paper experimentally shows evidence for binding, intercalation in the nick is proposed as a mode of genistein binding, and a model of the event is provided.

  DOI：

  10.1021/jm2007968

文献信息

• Genistein Binding Mode to Doubly Nicked Dumbbell DNA. Dynamic and Diffusion Ordered NMR Study
  作者：Karolina Hyz、Robert Kawęcki、Aleksandra Misior、Wojciech Bocian、Elżbieta Bednarek、Jerzy Sitkowski、Lech Kozerski

  DOI：10.1021/jm2007968

  日期：2011.12.22

  New genistein derivatives were synthesized, which are fairly well soluble in water, with respect to parent genistein, and thus facilitate study of the interaction with dumbbell DNA dodecamer, mimicking the biological target for topoisomerase II inhibitors. A pulsed field gradient spin echo NMR experiment was used to check the binding and to estimate the association constants and its pH dependence of genistein with dumbbell DNA. Experimental restraints based on nuclear Overhauser spectroscopy spectra were used to calculate the NMR structure in solution in case of 6,8-disubstituted genistein with dimethylaminomethyl groups and were used in molecular modeling calculations. The structure is dynamic, and 10 molecular dynamics runs yield a family of conformations that essentially differ in a depth of inclusion of genistein into a nick. The paper experimentally shows evidence for binding, intercalation in the nick is proposed as a mode of genistein binding, and a model of the event is provided.