dimethyl 6,9,10-tris(acetyloxy)benzo[kl]xanthene-1,2-dicarboxylate | 1273557-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: dimethyl 6,9,10-tris(acetyloxy)benzo[kl]xanthene-1,2-dicarboxylate
• 英文别名: Dimethyl 4,5,10-triacetyloxy-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-15,16-dicarboxylate
• CAS: 1273557-18-8
• 化学式: C₂₆H₂₀O₁₁
• 分子量: 508.438
• InChiKey: XLYFAIFJXISMMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  dimethyl 6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate 、 乙酸酐 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以96%的产率得到dimethyl 6,9,10-tris(acetyloxy)benzo[kl]xanthene-1,2-dicarboxylate
  参考文献：
  名称：

  Structural basis for the potential antitumour activity of DNA-interacting benzo[kl]xanthenelignans

  摘要：

  苯并[kl]氧杂蒽木脂素的生物特性及其在药理学上的应用在天然产物和合成化合物中非常罕见，几乎尚未被开发。在本研究中，我们采用STD-NMR和分子对接相结合的方法，研究了六种合成苯并[kl]氧杂蒽木脂素和天然代谢产物鲁菲西苷与DNA的可能相互作用，并同时对两种不同的癌细胞系（SW 480和HepG2）进行了体外生物测定，以评估其抗增殖活性。我们的数据表明，苯并[kl]氧杂蒽木脂素是设计具有潜在抗肿瘤特性的DNA选择性配体的合适先导化合物。

  DOI：

  10.1039/c0ob00480d

文献信息

• Structural basis for the potential antitumour activity of DNA-interacting benzo[kl]xanthenelignans
  作者：Simone Di Micco、Frédéric Mazué、Carmelo Daquino、Carmela Spatafora、Dominique Delmas、Norbert Latruffe、Corrado Tringali、Raffaele Riccio、Giuseppe Bifulco

  DOI：10.1039/c0ob00480d

  日期：——

  The biological properties and possible pharmacological applications of benzo[kl]xanthene lignans, rare among natural products and synthetic compounds, are almost unexplored. In the present contribution, the possible interaction of six synthetic benzo[kl]xanthene lignans and the natural metabolite rufescidride with DNA has been investigated through a combined STD-NMR and molecular docking approach, paralleled by in vitro biological assays on their antiproliferative activity towards two different cancer cell lines: SW 480 and HepG2. Our data suggest that the benzo[kl]xanthene lignans are suitable lead compounds for the design of DNA selective ligands with potential antitumour properties.

  苯并[kl]氧杂蒽木脂素的生物特性及其在药理学上的应用在天然产物和合成化合物中非常罕见，几乎尚未被开发。在本研究中，我们采用STD-NMR和分子对接相结合的方法，研究了六种合成苯并[kl]氧杂蒽木脂素和天然代谢产物鲁菲西苷与DNA的可能相互作用，并同时对两种不同的癌细胞系（SW 480和HepG2）进行了体外生物测定，以评估其抗增殖活性。我们的数据表明，苯并[kl]氧杂蒽木脂素是设计具有潜在抗肿瘤特性的DNA选择性配体的合适先导化合物。
• Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and <i>Candida</i> spp. growth inhibition
  作者：Carlo Genovese、Luana Pulvirenti、Nunzio Cardullo、Vera Muccilli、Gianna Tempera、Daria Nicolosi、Corrado Tringali

  DOI：10.1080/14786419.2018.1525375

  日期：2020.6.17

  In this work we synthetized the bioinspired benzoxanthene lignans (BXLs)3,14-22, and the phenazine derivative23as potential antimycotic agents. MICs and MFCs againstCandidastrains were determined. In a preliminary screening, compounds3,15,20,21,22were substantially inactive. Compounds14and17showed antifungal activity, being able to inhibit the growth of the majority ofCandidastrains with MIC values in the range 4.6-19.2 mu M (14) and 26.0-104.3 mu M (17); for three strains, the MICs were lower than those obtained using the antimycotic drug fluconazole. The three BXLs18,19and23showed some MIC values lower than that of fluconazole;18was also active against two non-albicans Candidastrains resistant to fluconazole. Phenazine23, although active only against one strain (MIC = 1.3 mu M), was one order of magnitude more potent than fluconazole. All the BXLs were fungicidal.