5-溴-2-哌啶基-1-甲基吡啶 | 364794-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-溴-2-哌啶基-1-甲基吡啶
• 中文别名: 5-溴-2-(哌啶-1-基甲基)吡啶
• 英文名称: 5-bromo-2-(1-piperidinylmethyl)pyridine
• 英文别名: 5-Bromo-2-(piperidin-1-ylmethyl)pyridine
• CAS: 364794-78-5
• 化学式: C₁₁H₁₅BrN₂
• 分子量: 255.157
• InChiKey: UQPUOJGAYLZKMH-UHFFFAOYSA-N

物化性质

• 沸点：
  300.1±27.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(4-methylsulfanyl-phenyl)-1,2,3,4-tetrahydro-isoquinolin-7-ol 、 5-溴-2-哌啶基-1-甲基吡啶 在 caesium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 生成 2-methyl-4-[4-(methylsulfanyl)phenyl]-7-[6-(piperidin-1-ylmethyl)pyridin-3-yloxy]-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Dual serotonin transporter inhibitor/histamine H3 antagonists: Development of rigidified H3 pharmacophores

  摘要：

  A series of tetrahydroisoquinolines acting as dual serotonin transporter inhibitor/histamine H-3 antagonists is described. The introduction of polar aromatic spacers as part of the histamine H-3 pharmacophore was explored. A convergent synthesis of the final products allowing late stage introduction of the aromatic side chain was developed. In vitro and in vivo data are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.017
• 作为产物：
  描述：

  二哌啶甲烷 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 5-溴-2-哌啶基-1-甲基吡啶
  参考文献：
  名称：

  Synthesis of 5-Bromopyridyl-2-magnesium Chloride and Its Application in the Synthesis of Functionalized Pyridines

  摘要：

  The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodomagnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was allowed to react with a variety of electrophiles to afford a range of useful functionalized pyridine derivatives. Application of this methodology to 5-bromo-2-iodo-3-picoline provided a simple and economical synthesis of a key intermediate for the preparation of Lonafarnib, a potent anticancer agent.

  DOI：

  10.1021/ol0400589

文献信息

• [EN] TETRAHYDROQUINOLINE DERIVATIVES AND THEIR PHARMACEUTICAL USE<br/>[FR] DÉRIVÉS DE TÉTRAHYDROQUINOLINE ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011054841A1

  公开（公告）日：2011-05-12

  Tetrahydroquinoline compounds of Formula (I) and salts thereof, pharmaceutical compositions containing such compounds and their use in therapy.

  Formula (I)的四氢喹啉化合物及其盐，含有这种化合物的药物组合物以及它们在治疗中的用途。
• Tetrahydroquinoline Derivatives And Their Pharmaceutical Use
  申请人：Demont Emmanuel Hubert

  公开号：US20120208798A1

  公开（公告）日：2012-08-16

  Tetrahydroquinoline compounds of formula (I) and salts thereof, pharmaceutical compositions containing such compounds and their use in therapy.

  公式（I）的四氢喹啉化合物及其盐，含有这种化合物的药物组合物以及它们在治疗中的用途。
• New (hetero)aryl compounds with MCH antagonistic activity and medicaments comprising these compounds
  申请人：Roth Juergen Gerald

  公开号：US20070111981A1

  公开（公告）日：2007-05-17

  The present invention relates to (hetero)aryl compounds of general formula I wherein the groups and radicals A, B, Q, W, X, Y, Z, R 1 , R 2 , R 4a , R 4b , R 5a , R 5b , have the meanings given in claim 1 . Moreover the invention relates to pharmaceutical compositions containing at least one compound according to the invention. By virtue of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia and diabetes.

  本发明涉及一般式I的（杂）芳基化合物，其中A、B、Q、W、X、Y、Z、R1、R2、R4a、R4b、R5a和R5b基团和基团具有权利要求1中给出的含义。此外，本发明涉及至少含有本发明中的一种化合物的制药组合物。由于其MCH受体拮抗活性，根据本发明的制药组合物适用于治疗代谢紊乱和/或进食障碍，尤其是肥胖症、贪食症、厌食症、暴食症和糖尿病。
• Tetrahydroquinoline derivatives and their pharmaceutical use
  申请人：Demont Emmanuel Hubert

  公开号：US08697725B2

  公开（公告）日：2014-04-15

  Tetrahydroquinoline compounds of formula (I) and salts thereof, pharmaceutical compositions containing such compounds and their use in therapy.

  公式（I）的四氢喹啉化合物及其盐，含有这种化合物的制药组合物及其在治疗中的用途。
• Mitigation of Acetylcholine Esterase Activity in the 1,7-Diazacarbazole Series of Inhibitors of Checkpoint Kinase 1
  作者：Lewis Gazzard、Karen Williams、Huifen Chen、Lorraine Axford、Elizabeth Blackwood、Brenda Burton、Kerry Chapman、Peter Crackett、Joy Drobnick、Charles Ellwood、Jennifer Epler、Michael Flagella、Emanuela Gancia、Matthew Gill、Simon Goodacre、Jason Halladay、Joanne Hewitt、Hazel Hunt、Samuel Kintz、Joseph Lyssikatos、Calum Macleod、Sarah Major、Guillaume Médard、Raman Narukulla、Judi Ramiscal、Stephen Schmidt、Eileen Seward、Christian Wiesmann、Ping Wu、Sharon Yee、Ivana Yen、Shiva Malek

  DOI：10.1021/acs.jmedchem.5b00464

  日期：2015.6.25

  Checkpoint kinase 1 (ChK1) plays a key role in the DNA damage response, facilitating cell-cycle arrest to provide sufficient time for lesion repair. This leads to the hypothesis that inhibition of ChK1 might enhance the effectiveness of DNA-damaging therapies in the treatment of cancer. Lead compound 1 (GNE-783), the prototype of the 1,7-diazacarbazole class of ChK1 inhibitors, was found to be a highly potent inhibitor of acetylcholine esterase (AChE) and unsuitable for development. A campaign of analogue synthesis established SAR delineating ChK1 and AChE activities and allowing identification of new leads with improved profiles. In silico docking using a model of AChE permitted rationalization of the observed SAR. Compounds 19 (GNE-900) and 30 (GNE-145) were identified as selective, orally bioavailable ChK1 inhibitors offering excellent in vitro potency with significantly reduced AChE activity. In combination with gemcitabine, these compounds demonstrate an in vivo pharmacodynamic effect and are efficacious in a mouse p53 mutant xenograft model.