11-hydroxy-2-(3-hydroxypropyl)anthra[9,1-de][1,3]oxazin-7(2H)-one | 1489168-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-hydroxy-2-(3-hydroxypropyl)anthra[9,1-de][1,3]oxazin-7(2H)-one
• 英文别名: 3-Hydroxy-15-(3-hydroxypropyl)-14-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one；3-hydroxy-15-(3-hydroxypropyl)-14-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one
• CAS: 1489168-91-3
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: JQHZTEBFCBBNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基-1-丁醇 、 1,8-二羟基蒽醌 在 吡啶 、 copper(I) bromide 作用下， 以58%的产率得到11-hydroxy-2-(3-hydroxypropyl)anthra[9,1-de][1,3]oxazin-7(2H)-one
  参考文献：
  名称：

  Synthesis, cytotoxicity and DNA binding of oxoazabenzo[de]anthracenes derivatives in colon cancer Caco-2 cells

  摘要：

  New oxoazabenzo[de]anthracenes derivatives were synthesised and characterised. Their interactions with calf thymus DNA were studied by UV spectrophotometric analysis and a competitive ethidium bromide displacement assay. Cytotoxicity was determined by MIT assay, against colon adenocarcinoma (Caco-2 cells). Among all the oxoazabenzo[delanthracenes derivatives reported herein only the piperidino derivative exhibited strong DNA binding properties and cytotoxic activity with IC50 values in the range of 16 +/- 1.5 mu M (72-h treatment). In addition, the piperidino derivative did not directly inhibit topoisomerase I and topoisomerase II enzymes. The results confirm that the presence of the oxoazabenzoldelanthracenes together with the piperidino functionality is crucial in exerting DNA binding and cytotoxic properties, hence demonstrating promise as a chemical scaffold for further development of new anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.038

文献信息

• Synthesis, cytotoxicity and DNA binding of oxoazabenzo[de]anthracenes derivatives in colon cancer Caco-2 cells
  作者：Alberto Di Salvo、Pauline Dugois、Delphine Tandeo、Marie Peltekian、Paul Kong Thoo Lin

  DOI：10.1016/j.ejmech.2013.08.038

  日期：2013.11

  New oxoazabenzo[de]anthracenes derivatives were synthesised and characterised. Their interactions with calf thymus DNA were studied by UV spectrophotometric analysis and a competitive ethidium bromide displacement assay. Cytotoxicity was determined by MIT assay, against colon adenocarcinoma (Caco-2 cells). Among all the oxoazabenzo[delanthracenes derivatives reported herein only the piperidino derivative exhibited strong DNA binding properties and cytotoxic activity with IC50 values in the range of 16 +/- 1.5 mu M (72-h treatment). In addition, the piperidino derivative did not directly inhibit topoisomerase I and topoisomerase II enzymes. The results confirm that the presence of the oxoazabenzoldelanthracenes together with the piperidino functionality is crucial in exerting DNA binding and cytotoxic properties, hence demonstrating promise as a chemical scaffold for further development of new anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.