methyl 3-(9-carbazolyl)propionate | 88107-73-7

• 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: methyl 3-(9-carbazolyl)propionate
• 英文别名: methyl 3-(9H-carbazol-9-yl)propanoate；3-carbazol-9-yl-propionic acid methyl ester；9-(βcarbomethoxyethyl)-carbazole；9H-Carbazole-9-propanoic acid, methyl ester；methyl 3-carbazol-9-ylpropanoate
• CAS: 88107-73-7
• 化学式: C₁₆H₁₅NO₂
• mdl: MFCD12559438
• 分子量: 253.301
• InChiKey: RURHUOBPXARERR-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  363.5±34.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(9-carbazolyl)propionate 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以47%的产率得到3-carbazol-9-yl-N-hydroxy-propionamide
  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：

  3-溴丙酸甲酯 、 咔唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.33h， 以49%的产率得到methyl 3-(9-carbazolyl)propionate
  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

文献信息

• Olefin-Oriented Selective Synthesis of Linear and Branched N-Alkylated Heterocycles by Hydroamination
  作者：Sushmita、Trapti Aggarwal、Kapil Mohan Saini、Akhilesh K. Verma

  DOI：10.1002/ejoc.202000373

  日期：2020.6.16

  Selective base‐Mediated hydroamination of N‐heterocycles with olefins for the construction of Linear and branched N‐alkylated heterocycles is described. This protocol provided the synthesis of exclusive N‐alkylated product instead of the C‐3 Michael addition product.

  描述了N-杂环与烯烃的选择性碱介导加氢胺化反应，用于构建直链和支链N-烷基化杂环。该协议提供了专有的N-烷基化产物而不是C-3 Michael加成产物的合成。
• Motuporamines, Anti-Invasion and Anti-Angiogenic Alkaloids from the Marine Sponge <i>Xestospongia </i><i>e</i><i>xigua </i>(Kirkpatrick):  Isolation, Structure Elucidation, Analogue Synthesis, and Conformational Analysis
  作者：David E. Williams、Kyle S. Craig、Brian Patrick、Lianne M. McHardy、Rob van Soest、Michel Roberge、Raymond J. Andersen

  DOI：10.1021/jo016101c

  日期：2002.1.1

  Single-crystal X-ray diffraction analysis of one of the analogues 20 showed that in the solid state its 16-membered macrocyclic amine fragment adopted the [4444] quadrangular conformation predicted by calculations to be the lowest energy conformation for the corresponding cycloalkane, cyclohexadecane. These data along with literature X-ray data and conformational analysis for derivatives of azacyclotridecane

  在新的抗入侵活性测定中，从巴布亚新几内亚收集到的海绵状外源Xestospongia exigua提取物呈阳性。生物测定指导的分馏导致鉴定了三种已知的莫托帕拉明A（1），B（2）和C（3）以及新的莫托帕拉明D（4），E（5）和F（6）以及G，H和I的混合物（15）。Motuporamines A（1），B（2）和C（3）以及G，H和I的混合物（15）负责粗提物的抗入侵活性。Motuporamine C（3）也被发现具有抗血管生成作用。已经合成了一系列motuporamines的类似物并评估了其抗侵袭活性。这些SAR结果表明，与天然motuporamine二胺侧链（13）融合的饱和15元环胺代表了该家族中抗侵袭活性的最佳结构。类似物20之一的单晶X射线衍射分析表明，在固态下，其16元大环胺片段采用[4444]四边形构象，该构象通过计算预测为相应的环烷烃环十六烷的最低能量构象。这些数据以及氮杂环
• 9-Substituted 3-aminocarbazole compounds
  申请人：Boehringer Mannheim G.m.b.H.

  公开号：US03975398A1

  公开（公告）日：1976-08-17

  Novel 3-aminocarbazole compounds of the formula: ##SPC1## Wherein X is hydrogen or halogen, Y is oxygen or represents two hydrogen atoms; and R.sub.1 and R.sub.2, which can be the same or different, are hydrogen, lower alkyl or hydroxyalkyl or amino; and n is 1 or 2, with the proviso that when n is 2, X, Y, R.sub.1 and R.sub.2 cannot all be hydrogen atoms, As well as the salts thereof with inorganic and organic acids; are outstandingly effective indicators for the determination of glucose and provide stable compositions for such glucose determination.

  化合物的中文翻译如下： 一种式子为：##SPC1##的新型3-氨基咔唑化合物，其中X为氢或卤素，Y为氧或代表两个氢原子；R.sub.1和R.sub.2可以相同也可以不同，为氢、低级烷基、羟基烷基或氨基；n为1或2，但当n为2时，X、Y、R.sub.1和R.sub.2不能全部为氢原子。此外，这些化合物与无机和有机酸的盐，对于葡萄糖的测定具有非常出色的效果，并提供了稳定的组成物。
• 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。