2-(2-[(methylsulfonyl)oxy]ethyl)-4-methyl-8,10-dimethoxy-anthra[1,9-cd]pyrazol-6(2H)-one | 914956-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(2-[(methylsulfonyl)oxy]ethyl)-4-methyl-8,10-dimethoxy-anthra[1,9-cd]pyrazol-6(2H)-one
• 英文别名: 2-(3,5-Dimethoxy-11-methyl-8-oxo-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-14-yl)ethyl methanesulfonate
• CAS: 914956-31-3
• 化学式: C₂₀H₂₀N₂O₆S
• 分子量: 416.455
• InChiKey: BOGYMECUVLHXDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-[(methylsulfonyl)oxy]ethyl)-4-methyl-8,10-dimethoxy-anthra[1,9-cd]pyrazol-6(2H)-one 、 N,N-二乙基乙二胺 在 盐酸 作用下， 以 乙醇 为溶剂， 以85%的产率得到2-[2-[(2-diethylaminoethyl)amino]ethyl]-4-methyl-8,10-dimethoxy-anthra[1,9-cd]pyrazol-6(2H)-one hydrochloride
  参考文献：
  名称：

  Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives

  摘要：

  A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.006
• 作为产物：
  描述：

  大黄素 在 potassium carbonate 、 三乙胺 作用下， 以 乙二醇乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 41.0h， 生成 2-(2-[(methylsulfonyl)oxy]ethyl)-4-methyl-8,10-dimethoxy-anthra[1,9-cd]pyrazol-6(2H)-one
  参考文献：
  名称：

  Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives

  摘要：

  A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.006

文献信息

• Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives
  作者：J.-H. Tan、Q.-X. Zhang、Z.-S. Huang、Y. Chen、X.-D. Wang、L.-Q. Gu、J.Y. Wu

  DOI：10.1016/j.ejmech.2006.04.006

  日期：2006.9

  A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity. (c) 2006 Elsevier SAS. All rights reserved.