12a-hydroxy-2,3,9-trimethoxy-11-oxiranylmethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one | 1331926-08-9

• 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: 12a-hydroxy-2,3,9-trimethoxy-11-oxiranylmethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
• 英文别名: (6aR,12aR)-12a-hydroxy-2,3,9-trimethoxy-11-(oxiran-2-ylmethoxy)-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• CAS: 1331926-08-9
• 化学式: C₂₂H₂₂O₉
• 分子量: 430.411
• InChiKey: PARVNALYTWPENR-HWGVQABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  12a-hydroxy-2,3,9-trimethoxy-11-oxiranylmethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 以70%的产率得到11-(3-chloro-2-hydroxy-propoxy)-12a-hydroxy-2,3,9-trimethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
  参考文献：
  名称：

  Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities

  摘要：

  6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase II alpha inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 mu M. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.052
• 作为产物：
  描述：

  6-deoxyclitoriracetal 、 环氧氯丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以40%的产率得到12a-hydroxy-2,3,9-trimethoxy-11-oxiranylmethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
  参考文献：
  名称：

  Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities

  摘要：

  6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase II alpha inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 mu M. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.052

文献信息

• Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities
  作者：Supranee Sangthong、Kuakarun Krusong、Nattaya Ngamrojanavanich、Tirayut Vilaivan、Songchan Puthong、Supajittra Chandchawan、Nongnuj Muangsin

  DOI：10.1016/j.bmcl.2011.06.052

  日期：2011.8

  6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase II alpha inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 mu M. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. (C) 2011 Elsevier Ltd. All rights reserved.