3a,4-dihydro-3a,8-dihydroxy-2,5-dimethyl-1,4-dioxaphenalene | 24506-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂非酮类
• 英文名称: 3a,4-dihydro-3a,8-dihydroxy-2,5-dimethyl-1,4-dioxaphenalene
• 英文别名: barakol；2,5-dimethyl-3aH-pyrano-[2,3,4-de]-1-benzopyran-3a,8-diol；3,7-dimethyl-2,6-dioxatricyclo[7.3.1.05,13]trideca-1(12),3,7,9(13),10-pentaene-5,11-diol
• CAS: 24506-68-1
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: LVPNMZHEDIKUFK-UHFFFAOYSA-N

物化性质

• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3a,4-dihydro-3a,8-dihydroxy-2,5-dimethyl-1,4-dioxaphenalene 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以32%的产率得到羟基甲基氧丙基苯并吡喃酮
  参考文献：
  名称：

  Transformation of barakol into cassiarins A, B, and their derivatives

  摘要：

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.053

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.
• Transformation of barakol into cassiarins A, B, and their derivatives
  作者：Sarawut Kanputhorn、Amorn Petsom、Patchanita Thamyongkit

  DOI：10.1016/j.tet.2010.07.053

  日期：2010.9

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.