7-hydroxy-4-nitro-2-phenethyl-2,3-dihydroisoindol-1-one | 474454-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 7-hydroxy-4-nitro-2-phenethyl-2,3-dihydroisoindol-1-one
• 英文别名: 7-hydroxy-4-nitro-2-(2-phenylethyl)-3H-isoindol-1-one
• CAS: 474454-54-1
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: MIZDHVNBAXDPAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-nitro-2-phenethyl-2,3-dihydroisoindol-1-one 在 palladium on activated charcoal 、 水 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 6.67h， 生成 4-[(2,5-dihydroxyphenyl)methylamino]-7-hydroxy-2-(2-phenylethyl)-3H-isoindol-1-one
  参考文献：
  名称：

  Synthesis and Investigation of Conformationally Restricted Analogues of Lavendustin A as Cytotoxic Inhibitors of Tubulin Polymerization

  摘要：

  A series of conformationally restricted analogues were synthesized in order to elucidate the possible effects of different amide conformations of lavendustin A derivatives on cytotoxicity in cancer cell cultures and on inhibition of tubulin polymerization. The conformationally restricted analogues were based on the oxazinedione and isoindolone ring systems. In addition, the amide bond was replaced by both cis and trans alkene moieties. Surprisingly, the results indicated very little effect of conformational. restriction on biological activity. Because all of the compounds synthesized had similar cytotoxicities and potencies as tubulin polymerization inhibitors, the side chain present on the aniline ring system does not appear to be important in the biological effects of the lavendustins. The hydroquinone ring of lavendustin A may be a more important determinant of the biological activity than the structure surrounding the aniline ring.

  DOI：

  10.1021/jm0202270
• 作为产物：
  描述：

  2,3-二甲基-4-硝基苯甲醚 在 chromium(VI) oxide 、 sodium hydroxide 、 potassium permanganate 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三溴化硼 、 三乙胺 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 45.5h， 生成 7-hydroxy-4-nitro-2-phenethyl-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  Synthesis and Investigation of Conformationally Restricted Analogues of Lavendustin A as Cytotoxic Inhibitors of Tubulin Polymerization

  摘要：

  A series of conformationally restricted analogues were synthesized in order to elucidate the possible effects of different amide conformations of lavendustin A derivatives on cytotoxicity in cancer cell cultures and on inhibition of tubulin polymerization. The conformationally restricted analogues were based on the oxazinedione and isoindolone ring systems. In addition, the amide bond was replaced by both cis and trans alkene moieties. Surprisingly, the results indicated very little effect of conformational. restriction on biological activity. Because all of the compounds synthesized had similar cytotoxicities and potencies as tubulin polymerization inhibitors, the side chain present on the aniline ring system does not appear to be important in the biological effects of the lavendustins. The hydroquinone ring of lavendustin A may be a more important determinant of the biological activity than the structure surrounding the aniline ring.

  DOI：

  10.1021/jm0202270

文献信息

• Synthesis and Investigation of Conformationally Restricted Analogues of Lavendustin A as Cytotoxic Inhibitors of Tubulin Polymerization
  作者：Fanrong Mu、Debbie J. Lee、Donald E. Pryor、Ernest Hamel、Mark Cushman

  DOI：10.1021/jm0202270

  日期：2002.10.1

  A series of conformationally restricted analogues were synthesized in order to elucidate the possible effects of different amide conformations of lavendustin A derivatives on cytotoxicity in cancer cell cultures and on inhibition of tubulin polymerization. The conformationally restricted analogues were based on the oxazinedione and isoindolone ring systems. In addition, the amide bond was replaced by both cis and trans alkene moieties. Surprisingly, the results indicated very little effect of conformational. restriction on biological activity. Because all of the compounds synthesized had similar cytotoxicities and potencies as tubulin polymerization inhibitors, the side chain present on the aniline ring system does not appear to be important in the biological effects of the lavendustins. The hydroquinone ring of lavendustin A may be a more important determinant of the biological activity than the structure surrounding the aniline ring.