6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester | 1239034-69-5

• 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
• 英文别名: 6-(2-methyl-1,2,3,4-tetrahydropyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester；methyl 6-(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)hexanoate
• CAS: 1239034-69-5
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: RLDGYYRSXORPMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid hydroxylamide
  参考文献：
  名称：

  Rational Design and Simple Chemistry Yield a Superior, Neuroprotective HDAC6 Inhibitor, Tubastatin A

  摘要：

  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.

  DOI：

  10.1021/ja102758v
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 硫酸 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 6-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)hexanoic acid methyl ester
  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

• HDAC INHIBITORS AND THERAPEUTIC METHODS OF USING SAME
  申请人：Kozikowski Alan

  公开号：US20120252740A1

  公开（公告）日：2012-10-04

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.

  本文披露了组蛋白去乙酰化酶抑制剂（HDACIs）及其含量。同时还披露了治疗疾病和状况的方法，其中抑制HDAC能够提供益处，如癌症、神经退行性疾病、神经系统疾病、创伤性脑损伤、中风、疟疾、自身免疫疾病、自闭症和炎症。
• HDAC Inhibitors and Therapeutic Methods of Using Same
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20130281484A1

  公开（公告）日：2013-10-24

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.

  本文披露了组蛋白去乙酰化酶抑制剂（HDACIs）及其组合物。同时还披露了治疗疾病和状况的方法，其中抑制HDAC可以提供益处，例如癌症、神经退行性疾病、神经系统疾病、创伤性脑损伤、中风、疟疾、自身免疫疾病、自闭症和炎症。
• HDAC inhibitors and therapeutic methods of using same
  申请人：Kozikowski Alan

  公开号：US08431538B2

  公开（公告）日：2013-04-30

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.

  本发明公开了组蛋白去乙酰化酶抑制剂（HDACIs）及其组合物。还公开了治疗疾病和条件的方法，其中抑制HDAC提供益处，如癌症、神经退行性疾病、神经疾病、创伤性脑损伤、中风、疟疾、自身免疫性疾病、自闭症和炎症。
• HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：The Board of Trustees of the University of Illinois

  公开号：EP2456757B1

  公开（公告）日：2019-05-01
• US8431538B2
  申请人：——

  公开号：US8431538B2

  公开（公告）日：2013-04-30