methyl 6-methoxy-2-methyl-3-nitrobenzoate | 474454-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 6-methoxy-2-methyl-3-nitrobenzoate
• CAS: 474454-48-3
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: ZGCIGDRCLHHRMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-methoxy-2-methyl-3-nitrobenzoate 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 37.0h， 生成 7-methoxy-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
• 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 、 硫酸 作用下， 以 甲醇 、 乙醇 、 正己烷 、 水 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 methyl 6-methoxy-2-methyl-3-nitrobenzoate
  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

• Tetracycline Derivatives with Reduced Antibiotic Activity and Neuroprotective Benefits
  申请人：Duncan Iain W.

  公开号：US20100009981A1

  公开（公告）日：2010-01-14

  The present disclosure is directed to compositions and methods which utilize the tetracycline scaffold, preferably the scaffold of tetracycline or minocycline, and which significantly lack antibiotic activity. The compounds have neuroprotective attributes without interfering with the drugs capacity to pass through the blood brain barrier. These compounds have neuroprotective activity because of their inhibition of neuronal cell cycle progression. The compounds are characterized in part by a fifth ring joining positions 9 and 10.

  本公开涉及利用四环素骨架的组合物和方法，优选是四环素或米诺环素的骨架，并且明显缺乏抗生素活性。这些化合物具有神经保护特性，而不会干扰药物通过血脑屏障的能力。这些化合物由于抑制神经元细胞周期进展而具有神经保护活性。这些化合物部分地以第五环连接9和10位置为特征。
• TETRACYCLINE DERIVATIVES WITH REDUCED ANTIBIOTIC ACTIVITY AND NEUROPROTECTIVE BENEFITS
  申请人：Neumedics

  公开号：US20130123217A1

  公开（公告）日：2013-05-16

  The present disclosure is directed to compositions and methods which utilize the tetracycline scaffold, preferably the scaffold of tetracycline or minocycline, and which significantly lack antibiotic activity. The compounds have neuroprotective attributes without interfering with the drugs capacity to pass through the blood brain barrier. These compounds have neuroprotective activity because of their inhibition of neuronal cell cycle progression. The compounds are characterized in part by a fifth ring joining positions 9 and 10.
• US8338477B2
  申请人：——

  公开号：US8338477B2

  公开（公告）日：2012-12-25
• US9168265B2
  申请人：——

  公开号：US9168265B2

  公开（公告）日：2015-10-27
• US9573912B2
  申请人：——

  公开号：US9573912B2

  公开（公告）日：2017-02-21