7,8-dimethoxyphenanthridine | 41001-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7,8-dimethoxyphenanthridine
• 英文别名: 7,8-dimethoxy-phenanthridine；7,8-Dimethoxy-phenanthridin
• CAS: 41001-80-3
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: FDKOFTWFAPBJNI-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  407.5±25.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxyphenanthridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 7,8-dimethoxyphenanthridine-5-oxide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

  摘要：

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.

  DOI：

  10.1021/jm8005433
• 作为产物：
  描述：

  3',4'-dimethoxy-[1,1'-biphenyl]-2-amine 、 N,N-二甲基甲酰胺 在 正丁基锂 、 水 作用下， 生成 7,8-dimethoxyphenanthridine
  参考文献：
  名称：

  锂化反应的合成应用-十四：7,8-二甲氧基菲啶的新颖合成

  摘要：

  通过有机锂化反应以简单的步骤并且以良好的收率合成了难以获得的7，8-二甲氧基菲啶。

  DOI：

  10.1016/s0040-4020(01)97703-8

文献信息

• NARASIMHAN N. S.; CHANDRACHOOD P. S.; SHETE N. R., TETRAHEDRON, 1981, 37, NO 4, 825-827
  作者：NARASIMHAN N. S.、 CHANDRACHOOD P. S.、 SHETE N. R.

  DOI：——

  日期：——
• Synthetic application of lithiation reactions—xiv
  作者：N.S. Narasimhan、P.S. Chandrachood、N.R. Shete

  DOI：10.1016/s0040-4020(01)97703-8

  日期：1981.1

  The difficultly accessible 7,8-dimethoxy phenanthridine has been synthesised by organolithiation reaction in simple steps and in good yield.

  通过有机锂化反应以简单的步骤并且以良好的收率合成了难以获得的7，8-二甲氧基菲啶。
• Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors
  作者：Paul H. Bernardo、Kah-Fei Wan、Thirunavukkarasu Sivaraman、Jin Xu、Felicity K. Moore、Alvin W. Hung、Henry Y. K. Mok、Victor C. Yu、Christina L. L. Chai

  DOI：10.1021/jm8005433

  日期：2008.11.13

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.