5-羟基-2-甲氧基-吡啶-3-甲醛 | 867267-31-0

• 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-羟基-2-甲氧基-吡啶-3-甲醛
• 英文名称: 5-hydroxy-2-methoxynicotinaldehyde
• 英文别名: 5-Hydroxy-2-methoxypyridine-3-carbaldehyde
• CAS: 867267-31-0
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: DJBIGOABNHRDPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-羟基-2-甲氧基-吡啶-3-甲醛 在 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 (2,5-dimethoxypyridin-3-yl)methanol
  参考文献：
  名称：

  [EN] ANTIBACTERIAL COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS ANTIBACTÉRIENS ET UTILISATIONS DE CEUX-CI

  摘要：

  本发明涉及式(I)的化合物，包括其任何立体化异构体或其药学上可接受的盐，用于治疗结核病。

  公开号：

  WO2017155909A1
• 作为产物：
  描述：

  2-methoxy-5-(triisopropylsilanyloxy)pyridine 在 四丁基氟化铵 、 甲基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 5-羟基-2-甲氧基-吡啶-3-甲醛
  参考文献：
  名称：

  A Regioselective Route to 5- and 6-Azaindoles

  摘要：

  成功以区域选择性的方法合成了4,7-二甲氧基5-和6-氮杂吲哚，这是一种在最近开发的抗HIV-1药物中存在的结构单元。所开发的策略基于在锂介导的甲酰化步骤中适当选择保护基团，随后进行叠氮丙烯酸酯的热环化。

  DOI：

  10.1055/s-2005-871946

文献信息

• Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles
  作者：Zahia Mahiout、Thierry Lomberget、Sylvie Goncalves、Roland Barret

  DOI：10.1039/b719776d

  日期：——

  towards BBr3-mediated selective monodemethylation and oxidative demethylation reactions were also investigated. The regioselectivity of the deprotection was confirmed using a chemical approach. Oxidation reactions were then carried out on either dimethoxy- or hydroxymethoxyazaindoles, in different solvents, using [bis(trifluoroacetoxy)iodo]benzene. In acetonitrile-water, trioxopyrrolopyridines 12 were obtained

  的4,7-二甲氧基-5-和6-氮杂吲哚2所述的区域选择性合成已经实现，基于邻位定向或邻排斥基团在吡啶环的甲酰化的合适的选择。本文描述了甲酰化步骤的区域选择性和叠氮基丙烯酸酯中间体4的制备的研究。还研究了5和6氮杂吲哚结构对BBr3介导的选择性单脱甲基和氧化脱甲基反应的反应性。使用化学方法证实了脱保护基的区域选择性。然后使用[双（三氟乙酰氧基）碘]苯在不同的溶剂中对二甲氧基-或羟基甲氧基氮杂吲哚进行氧化反应。在乙腈水中，制得三氧杂吡咯烷吡啶12 而在乙腈-甲醇中观察到官能化的氮吲哚17的形成。X射线衍射分析证明了三氧杂吡咯并吡啶的互变异构结构。
• Antibacterial compounds and uses thereof
  申请人：The Global Alliance for TB Drug Development, Inc.

  公开号：US10508097B2

  公开（公告）日：2019-12-17

  The present invention relates to compounds of formula (I) including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

  本发明涉及用于治疗结核病的式 (I) 化合物，包括其任何立体化学异构体形式，或其药学上可接受的盐类。
• 3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel
  作者：Hamish S. Sutherland、Amy S.T. Tong、Peter J. Choi、Adrian Blaser、Daniel Conole、Scott G. Franzblau、Manisha U. Lotlikar、Christopher B. Cooper、Anna M. Upton、William A. Denny、Brian D. Palmer

  DOI：10.1016/j.bmc.2019.02.026

  日期：2019.4

  Bedaquiline is a new drug of the diarylquinoline class that has proven to be clinically effective against drugresistant tuberculosis, but has a cardiac liability (prolongation of the QT interval) due to its potent inhibition of the cardiac potassium channel protein hERG. Bedaquiline is highly lipophilic and has an extremely long terminal half-life, so has the potential for more-than-desired accumulation in tissues during the relatively long treatment durations required to cure TB. The present work is part of a program that seeks to identify a diarylquinoline that is as potent as bedaquiline against Mycobacterium tuberculosis, with lower lipophilicity, higher clearance, and lower risk for QT prolongation. Previous work led to the identification of compounds with greatly-reduced lipophilicity compounds that retain good anti-tubercular activity in vitro and in mouse models of TB, but has not addressed the hERG blockade. We now present compounds where the C-unit naphthalene is replaced by a 3,5dialkoxy- 4-pyridyl, demonstrate more potent in vitro and in vivo anti-tubercular activity, with greatly attenuated hERG blockade. Two examples of this series are in preclinical development.
• ANTIBACTERIAL COMPOUNDS AND USES THEREOF
  申请人：The Global Alliance for TB Drug Development, Inc.

  公开号：EP3426255A1

  公开（公告）日：2019-01-16