diethyl 6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate | 1596209-98-1

• 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: diethyl 6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate
• 英文别名: Diethyl 4,5,10-trihydroxy-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-15,16-dicarboxylate；diethyl 4,5,10-trihydroxy-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-15,16-dicarboxylate
• CAS: 1596209-98-1
• 化学式: C₂₂H₁₈O₈
• 分子量: 410.38
• InChiKey: NDINJAAUQRTQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  咖啡酸乙酯 在 manganese triacetate 作用下， 以 氯仿 为溶剂， 生成 diethyl 6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate
  参考文献：
  名称：

  Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and Candida spp. growth inhibition

  摘要：

  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.

  DOI：

  10.1080/14786419.2018.1525375

文献信息

• Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties
  作者：Carmela Spatafora、Vincenza Barresi、Vedamurthy M. Bhusainahalli、Simone Di Micco、Nicolò Musso、Raffaele Riccio、Giuseppe Bifulco、Daniele Condorelli、Corrado Tringali

  DOI：10.1039/c3ob42521e

  日期：——

  In this work twelve benzo[k,l]xanthene lignans were synthesized by biomimetic, Mn-mediated oxidative coupling of caffeic esters and amides. These compounds, bearing different flexible pendants at position C1/C2 of the aromatic core, interact with DNA in a dual mode, as confirmed by DF-STD NMR analysis and molecular docking: the planar core acts as a base pair intercalant, whereas the flexible pendants

  在这项工作中，通过仿生，锰介导的咖啡酸酯和酰胺的氧化偶联，合成了十二种苯并[ k，l ]氧杂蒽木酚聚糖。这些化合物在芳族核的C1 / C2位置带有不同的柔性侧基，通过DF-STD NMR分析和分子对接证实，其以双模式与DNA相互作用：平面核充当碱基对嵌入剂，而柔性吊坠用作小凹槽活页夹。在一组六种肿瘤细胞系中评估了它们的抗增殖活性：HT-29，Caco-2，HCT-116（人结肠癌），H226，A549（人肺癌）和SH-SY5Y（人神经母细胞瘤）。除29种化合物外，所有正在研究的化合物均具有针对一种或多种细胞系以及明显的亲脂性酯的活性。13和28表现出最高的活性。化合物13对HCT-116（结肠，GI 50 = 3.16μM）和H226（肺，GI 50 = 4.33μM）细胞系比抗癌药物5-氟尿嘧啶（5-FU）具有更高的活性。
• 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.