1,3,8-Trihydroxy-6-methyl-2-[(4-methylpiperazin-1-yl)methyl]anthracene-9,10-dione | 1472625-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,8-Trihydroxy-6-methyl-2-[(4-methylpiperazin-1-yl)methyl]anthracene-9,10-dione
• 英文别名: 1,3,8-trihydroxy-6-methyl-2-[(4-methylpiperazin-1-yl)methyl]anthracene-9,10-dione
• CAS: 1472625-25-4
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: ROJMCEZKCOYBMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 大黄素 在 溶剂黄146 作用下， 反应 4.0h， 生成 1,3,8-Trihydroxy-6-methyl-2-[(4-methylpiperazin-1-yl)methyl]anthracene-9,10-dione
  参考文献：
  名称：

  Preparation of novel antiproliferative emodin derivatives and studies on their cell cycle arrest, caspase dependent apoptosis and DNA binding interaction

  摘要：

  Emodin (1) is the major bioactive compound of several herb species, which belongs to anthraquinone class of compound. As a part of our drug discovery program, large quantities of emodin (1) was isolated from the roots of Rheum emodi and a library of novel emodin derivatives 2-15 were prepared to evaluate their antiproliferative activities against HepG2, MDA-MB-231 and NIH/3T3 cells lines. The derivatives 3 and 12 strongly inhibited the proliferation of HepG2 and MDA-MB-231 cancer cell line with an IC50 of 5.6, 13.03 and 10.44, 5.027, respectively, which is comparable to marketed drug epirubicin (III). The compounds 3 and 12 were also capable of inducing cell cycle arrest and caspase dependent apoptosis in HepG2 cell lines and exhibit DNA intercalating activity. These emodin derivatives hold promise for developing safer alternatives to the marketed epirubicin. (C) 2013 Elsevier GmbH. All rights reserved.

  DOI：

  10.1016/j.phymed.2013.03.015

文献信息

• Preparation of novel antiproliferative emodin derivatives and studies on their cell cycle arrest, caspase dependent apoptosis and DNA binding interaction
  作者：T. Narender、P. Sukanya、Komal Sharma、Surendar Reddy Bathula

  DOI：10.1016/j.phymed.2013.03.015

  日期：2013.7

  Emodin (1) is the major bioactive compound of several herb species, which belongs to anthraquinone class of compound. As a part of our drug discovery program, large quantities of emodin (1) was isolated from the roots of Rheum emodi and a library of novel emodin derivatives 2-15 were prepared to evaluate their antiproliferative activities against HepG2, MDA-MB-231 and NIH/3T3 cells lines. The derivatives 3 and 12 strongly inhibited the proliferation of HepG2 and MDA-MB-231 cancer cell line with an IC50 of 5.6, 13.03 and 10.44, 5.027, respectively, which is comparable to marketed drug epirubicin (III). The compounds 3 and 12 were also capable of inducing cell cycle arrest and caspase dependent apoptosis in HepG2 cell lines and exhibit DNA intercalating activity. These emodin derivatives hold promise for developing safer alternatives to the marketed epirubicin. (C) 2013 Elsevier GmbH. All rights reserved.