3,7-Dimethyl-11-phenylselanyloxy-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(13),3,5,7,9,11-hexaene | 1613033-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3,7-Dimethyl-11-phenylselanyloxy-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(13),3,5,7,9,11-hexaene
• 英文别名: 3,7-dimethyl-11-phenylselanyloxy-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(13),3,5,7,9,11-hexaene
• CAS: 1613033-13-8
• 化学式: C₁₉H₁₅NO₂Se
• 分子量: 368.294
• InChiKey: DFODLKVAVUJDII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3a,4-dihydro-3a,8-dihydroxy-2,5-dimethyl-1,4-dioxaphenalene 在 氯化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,7-Dimethyl-11-phenylselanyloxy-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(13),3,5,7,9,11-hexaene
  参考文献：
  名称：

  Synthesis, cytotoxicity, DNA binding and topoisomerase II inhibition of cassiarin A derivatives

  摘要：

  Four series of cassiarin A derivatives with alkanoyl (3a-3d), aroyl (4a-4d), hydroxy/amino-substituted ethylene glycol (5a-5c) and selenium-containing (6a) side chains were synthesized. Their antitumor activities were evaluated against BT474, CHAGO, HepG2, KATO-III, SW620 and CaSki cancer cell lines. Preliminary results demonstrated that 5b had moderate activities against HepG2 and KATO-III cell lines, while 5c showed moderate to high cytotoxicity against most tested cell lines. In addition, 6a exhibited moderate cytotoxicity against cervical cells, CaSki. DNA-binding and ethidium bromide displacement experiments suggested that 5c and 5b binds to DNA via an intercalative mode, whereas 6a did not. However, the selenium-containing cassiarin A derivative 6a inhibited topoisomerase II with more than 95% inhibition at the concentration of 50 mu M. These cassiarin A derivatives showed lower toxicity to normal cells, WI-38 than amonafide therefore they are potential lead compounds to be further developed as new anticancer agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.107

文献信息

• Synthesis, cytotoxicity, DNA binding and topoisomerase II inhibition of cassiarin A derivatives
  作者：Urarika Luesakul、Tanapat Palaga、Kuakarun Krusong、Nattaya Ngamrojanavanich、Tirayut Vilaivan、Songchan Puthong、Nongnuj Muangsin

  DOI：10.1016/j.bmcl.2014.04.107

  日期：2014.7

  Four series of cassiarin A derivatives with alkanoyl (3a-3d), aroyl (4a-4d), hydroxy/amino-substituted ethylene glycol (5a-5c) and selenium-containing (6a) side chains were synthesized. Their antitumor activities were evaluated against BT474, CHAGO, HepG2, KATO-III, SW620 and CaSki cancer cell lines. Preliminary results demonstrated that 5b had moderate activities against HepG2 and KATO-III cell lines, while 5c showed moderate to high cytotoxicity against most tested cell lines. In addition, 6a exhibited moderate cytotoxicity against cervical cells, CaSki. DNA-binding and ethidium bromide displacement experiments suggested that 5c and 5b binds to DNA via an intercalative mode, whereas 6a did not. However, the selenium-containing cassiarin A derivative 6a inhibited topoisomerase II with more than 95% inhibition at the concentration of 50 mu M. These cassiarin A derivatives showed lower toxicity to normal cells, WI-38 than amonafide therefore they are potential lead compounds to be further developed as new anticancer agents. (C) 2014 Elsevier Ltd. All rights reserved.