5,8-dimethoxy-4a,9,9a,10-tetrahydro-9,10-[o]benzenoanthracene-1,4-dione | 600736-18-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 5,8-dimethoxy-4a,9,9a,10-tetrahydro-9,10-[o]benzenoanthracene-1,4-dione
• 英文别名: 4a,9,9a,10-Tetrahydro-5,8-dimethoxy-9,10-<1',2'>benzenoanthracen-1,4-dion；10,13-Dimethoxypentacyclo[6.6.6.02,7.09,14.015,20]icosa-4,9,11,13,15,17,19-heptaene-3,6-dione；10,13-dimethoxypentacyclo[6.6.6.02,7.09,14.015,20]icosa-4,9,11,13,15,17,19-heptaene-3,6-dione
• CAS: 600736-18-3
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: ATMGCGBOWAIEEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxy-4a,9,9a,10-tetrahydro-9,10-[o]benzenoanthracene-1,4-dione 在 碘苯二乙酸 、 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 9,10-dihydro-5,8-dimethoxy-1,2,4-tris-acetoxy-9,10-[o]benzenoanthracene
  参考文献：
  名称：

  Synthesis and activity on free radical processes and inflammation of 9,10-dihydro-5,8-dimethoxy-triptycene-quinones

  摘要：

  Three triptycene quinones bearing methoxy groups were prepared following a Diels-Alder methodology and were evaluated for antioxidant and anti-inflammatory activity bearing in mind their structural features that could justify intervention with free radical processes. Improved synthetic pathways were achieved for target molecules 9,10-dihydro-5,8-dimethoxy-9,10-[o]benzenoanthracene-1.4-dione (4), 9,10-dihydro-2-hydroxy-5,8-dimethoxy-9,10-[o]benzenoanthracene-1,4-dione (6), and 9,10-dihydro-2,5,8-trimethoxy-9,10-[o]benzenoanthracene-1,4-dione (9). Under our experimental conditions these compounds showed very significant antioxidant activity offering protection against lipid peroxidation of rat hepatic microsomal fraction while inhibiting the reaction completely at very low concentrations (12.5-80 muM). Moreover, compound 6 that was examined, inhibited by 44% (at 120 muM) lipoxygenase acitvity while the anti-inflammatory activity of the compounds, as assessed by the reduction of the mouse paw edema induced by Freund's complete adjuvant, was significant and comparable to that of indomethacin. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00078-3
• 作为产物：
  描述：

  1,4-二甲氧基-9,10-二氢蒽-9,10-二醇 以 二乙二醇二甲醚 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 7.0h， 生成 5,8-dimethoxy-4a,9,9a,10-tetrahydro-9,10-[o]benzenoanthracene-1,4-dione
  参考文献：
  名称：

  Quast, Helmut; Fuchsbauer, Hans-Lothar, Chemische Berichte, 1986, vol. 119, # 3, p. 1016 - 1038

  摘要：

  DOI：

文献信息

• Quast, Helmut; Fuchsbauer, Hans-Lothar, Chemische Berichte, 1986, vol. 119, # 3, p. 1016 - 1038
  作者：Quast, Helmut、Fuchsbauer, Hans-Lothar

  DOI：——

  日期：——
• Synthesis and activity on free radical processes and inflammation of 9,10-dihydro-5,8-dimethoxy-triptycene-quinones
  作者：N Xanthopoulou

  DOI：10.1016/s0223-5234(03)00078-3

  日期：2003.6

  Three triptycene quinones bearing methoxy groups were prepared following a Diels-Alder methodology and were evaluated for antioxidant and anti-inflammatory activity bearing in mind their structural features that could justify intervention with free radical processes. Improved synthetic pathways were achieved for target molecules 9,10-dihydro-5,8-dimethoxy-9,10-[o]benzenoanthracene-1.4-dione (4), 9,10-dihydro-2-hydroxy-5,8-dimethoxy-9,10-[o]benzenoanthracene-1,4-dione (6), and 9,10-dihydro-2,5,8-trimethoxy-9,10-[o]benzenoanthracene-1,4-dione (9). Under our experimental conditions these compounds showed very significant antioxidant activity offering protection against lipid peroxidation of rat hepatic microsomal fraction while inhibiting the reaction completely at very low concentrations (12.5-80 muM). Moreover, compound 6 that was examined, inhibited by 44% (at 120 muM) lipoxygenase acitvity while the anti-inflammatory activity of the compounds, as assessed by the reduction of the mouse paw edema induced by Freund's complete adjuvant, was significant and comparable to that of indomethacin. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.