6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester trifluoroacetic acid salt | 1239034-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester trifluoroacetic acid salt
• 英文别名: 6-(2-methyl-1,2,3,4-tetrahydropyrido[4,3-b]indol-5-yl)hexanoic acid hydroxyamide, trifluoroacetic acid salt；N-hydroxy-6-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)hexanamide;2,2,2-trifluoroacetic acid
• CAS: 1239034-60-6
• 化学式: C₂HF₃O₂*C₁₈H₂₅N₃O₂
• 分子量: 429.439
• InChiKey: NZABLXDQXUNASA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 在 盐酸羟胺 、 potassium tert-butylate 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester trifluoroacetic acid salt
  参考文献：
  名称：

  [EN] HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  [FR] INHIBITEURS DE HDAC ET PROCÉDÉS THÉRAPEUTIQUES LES UTILISANT

  摘要：

  公开号：

  WO2011011186A3

文献信息

• Rational Design and Simple Chemistry Yield a Superior, Neuroprotective HDAC6 Inhibitor, Tubastatin A
  作者：Kyle V. Butler、Jay Kalin、Camille Brochier、Guilio Vistoli、Brett Langley、Alan P. Kozikowski

  DOI：10.1021/ja102758v

  日期：2010.8.11

  Structure-based drug design combined with homology modeling techniques were used to develop potent inhibitors of HDAC6 that display superior selectivity for the HDAC6 isozyme compared to other inhibitors. These inhibitors can be assembled in a few synthetic steps, and thus are readily scaled up for in vivo studies. An optimized compound from this series, designated Tubastatin A, was tested in primary cortical neuron cultures in which it was found to induce elevated levels of acetylated a-tubulin, but not histone, consistent with its HDAC6 selectivity. Tubastatin A also conferred dose-dependent protection in primary cortical neuron cultures against glutathione depletion-induced oxidative stress. Importantly, when given alone at all concentrations tested, this hydroxamate-containing HDAC6-selective compound displayed no neuronal toxicity, thus, forecasting the potential application of this agent and its analogues to neurodegenerative conditions.
• [EN] HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME<br/>[FR] INHIBITEURS DE HDAC ET PROCÉDÉS THÉRAPEUTIQUES LES UTILISANT
  申请人：UNIV ILLINOIS

  公开号：WO2011011186A3

  公开（公告）日：2011-05-26