(4S,17R,23R,36S)-18,18,37,37-tetramethyl-15,19,34,38-tetraoxanonacyclo[20.16.0.03,20.04,17.05,14.06,11.023,36.024,33.025,30]octatriaconta-1(22),3(20),5(14),6,8,10,12,24(33),25,27,29,31-dodecaene-2,21-dione | 1082067-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (4S,17R,23R,36S)-18,18,37,37-tetramethyl-15,19,34,38-tetraoxanonacyclo[20.16.0.03,20.04,17.05,14.06,11.023,36.024,33.025,30]octatriaconta-1(22),3(20),5(14),6,8,10,12,24(33),25,27,29,31-dodecaene-2,21-dione
• CAS: 1082067-81-9
• 化学式: C₃₈H₃₂O₆
• 分子量: 584.668
• InChiKey: MRVPWQBDSODAPL-BMAQFFHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  44
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 、 2-(3-methylbut-2-enyloxy)naphthalene-1-carbaldehyde 在 ethylenediamine Tetraacetic Acid 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以35.8%的产率得到
  参考文献：
  名称：

  Bis-pyranobenzoquinones as a New Family of Reversal Agents of the Multidrug Resistance Phenotype Mediated by P-Glycoprotein in Mammalian Cells and the Protozoan Parasite Leishmania

  摘要：

  We have synthesized a set of bis-pyranobenzoquinones through a direct and highly efficient approach based on a double intramolecular domino Knoevenagel hetero Diels-Alder reaction. These bis-pyranobenzoquinone derivatives are compounds whose skeletons have similarities to those of some anticancerous and leishmanicidal drugs. Considering that these drugs are substrates for some members of the ATP-binding cassette (ABC) family of proteins that confers a multidrug resistance (MDR) phenotype, we have carried out the biological evaluation of 20 bis-pyranobenzoquinones as modulators of the MDR phenotype in mammalian cell lines overexpressing P-glycoprotein, MRP1, or BCRP. Moreover, we also tested some of these compounds as potential MDR modulators in a Leishmania tropica line overexpressing a P-glycoprotein-like transporter. Compounds 9 and 10 are, in this work, the most promising reversal agents of MDR in human cancer cell lines, while compounds 4 and 20 showed potent reversal activity of MDR phenotype in the protozoan parasite Leishmania.

  DOI：

  10.1021/jm800403b

文献信息

• Bis-pyranobenzoquinones as a New Family of Reversal Agents of the Multidrug Resistance Phenotype Mediated by P-Glycoprotein in Mammalian Cells and the Protozoan Parasite <i>Leishmania</i>
  作者：Sandra Jiménez-Alonso、Antonio L. Pérez-Lomas、Ana Estévez-Braun、Francisco Muñoz Martinez、Haydee Chávez Orellana、Angel G. Ravelo、Francisco Gamarro、Santiago Castanys、Matías López

  DOI：10.1021/jm800403b

  日期：2008.11.27

  We have synthesized a set of bis-pyranobenzoquinones through a direct and highly efficient approach based on a double intramolecular domino Knoevenagel hetero Diels-Alder reaction. These bis-pyranobenzoquinone derivatives are compounds whose skeletons have similarities to those of some anticancerous and leishmanicidal drugs. Considering that these drugs are substrates for some members of the ATP-binding cassette (ABC) family of proteins that confers a multidrug resistance (MDR) phenotype, we have carried out the biological evaluation of 20 bis-pyranobenzoquinones as modulators of the MDR phenotype in mammalian cell lines overexpressing P-glycoprotein, MRP1, or BCRP. Moreover, we also tested some of these compounds as potential MDR modulators in a Leishmania tropica line overexpressing a P-glycoprotein-like transporter. Compounds 9 and 10 are, in this work, the most promising reversal agents of MDR in human cancer cell lines, while compounds 4 and 20 showed potent reversal activity of MDR phenotype in the protozoan parasite Leishmania.