5-溴-2-甲基-3-苄氧基-4-吡啶酮 | 1421314-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-溴-2-甲基-3-苄氧基-4-吡啶酮
• 英文名称: 3-benzyloxy-5-bromo-2-methyl-pyridin-4-ol
• 英文别名: 3-(Benzyloxy)-5-bromo-2-methyl-4-pyridinol；5-bromo-2-methyl-3-phenylmethoxy-1H-pyridin-4-one
• CAS: 1421314-64-8；906657-86-1
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: RTPDVDCGESIMNA-UHFFFAOYSA-N

物化性质

• 沸点：
  419.4±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲基-3-苄氧基-4-吡啶酮 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 甲醇 、 manganese(IV) oxide 、 sodium hydroxide 、 sodium chlorite 、 potassium osmate(VI) 、 sodium periodate 、 氨基磺酸 、 水 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.04h， 生成 (12S)-N-[(4-fluorophenyl)methyl]-4-hydroxy-11,12-dimethyl-2,5-dioxo-1,8,11-triazatricyclo[8.5.0.03,8]pentadeca-3,6-diene-6-carboxamide
  参考文献：
  名称：

  WO2006/116764

  摘要：

  公开号：
• 作为产物：
  描述：

  麦芽醇 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.5h， 生成 5-溴-2-甲基-3-苄氧基-4-吡啶酮
  参考文献：
  名称：

  [EN] TRICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS
  [FR] COMPOSÉS TRICYCLIQUES À TITRE D'INHIBITEURS DE LA MPGES-1

  摘要：

  本公开涉及式(I)的化合物及其药学上可接受的盐，作为m PGES-1抑制剂。这些化合物是微粒体前列腺素E合成酶-1（m PGES-1）酶的抑制剂，因此在治疗来自多种疾病或状况的疼痛和/或炎症方面非常有用，如哮喘、骨关节炎、风湿性关节炎、急性或慢性疼痛和神经退行性疾病。

  公开号：

  WO2013153535A1

文献信息

• The Synthesis of 5-Functional 3-Hydroxypyridin-4-ones and Their Impact on the Chelating Properties of the Ligands
  作者：Yu-Lin Chen、Jing Chen、Yongmin Ma、Robert C. Hider

  DOI：10.1246/cl.141133

  日期：2015.4.5

  The presence of the 5-functional group on 3-hydroxypyridin-4-ones (HPOs) can significantly change their chelating properties because the 5-position is adjacent to one of the chelating moieties. A 5-methoxy-substituted HPO has been successfully synthesized using a 5-bromo analogue with NaOMe in the presence of a copper(I) catalyst. The atomic charges and stability constants of the HPOs with either electron-donating or election-withdrawing groups on the 5-position were compared. The result showed that the 5-substituted HPOs possess lower stability constants, compared to those of the 5-unsubstituted analogue (deferiprone).

  3-hydroxypyridin-4-ones (HPOs)上 5-官能团的存在会显著改变其螯合特性，因为 5-位与螯合分子之一相邻。在铜（I）催化剂存在下，利用 5-溴类似物与 NaOMe 成功合成了 5-甲氧基取代的 HPO。比较了在 5 位上带有电子捐赠基团或选举撤回基团的 HPO 的原子电荷和稳定常数。结果表明，与 5 位未取代的类似物（去铁酮）相比，5 位取代的 HPO 具有较低的稳定性常数。
• Polycyclic carbamoylpyridone derivative having hiv integrase inhibitory activity
  申请人：Johns Brian Alvin

  公开号：US20090318421A1

  公开（公告）日：2009-12-24

  The present invention is to provide a novel compound (I) shown below, having the anti-virus activity, particularly the HIV integrase inhibitory activity, and a drug containing the same, particularly an anti-HIV drug, as well as a process and an intermediate thereof. (wherein Z 1 is NR 4 ; R 1 is hydrogen or lower alkyl; X is a single bond, a hetero atom group selected from O, S, SO, SO 2 and NH, or lower alkylene or lower alkenylene in which the hetero atom group may intervene; R 2 is optionally substituted aryl; R 3 is hydrogen, a halogen, hydroxy, optionally substituted lower alkyl etc; and R 4 and Z 2 part taken together forms a ring, to form a polycyclic compound, including e.g., a tricyclic or tetracyclic compound.

  本发明提供了一种新型化合物(I)，如下所示，具有抗病毒活性，特别是HIV整合酶抑制活性，以及含有该化合物的药物，特别是抗HIV药物，以及其制备方法和中间体。(其中Z1为NR4;R1为氢或低碳基;X为单键，从O、S、SO、SO2和NH中选择的杂原子基团，或低碳基或低碳烯基，在其中杂原子基团可以介入;R2为可选取代芳基;R3为氢、卤素、羟基、可选取代的低碳基等;R4和Z2共同形成环，形成多环化合物，包括例如三环或四环化合物。
• Bicyclic Carbamoylpyridone Derivative Having Hiv Integrase Inhibitory Activity
  申请人：Yoshida Hiroshi

  公开号：US20080161271A1

  公开（公告）日：2008-07-03

  [Object] Is to provide a novel compound having an anti-viral activity, particularly a HIV integrase inhibitory activity, and an agent, particularly an anti-HIV agent. [Solving means] A compound represented by the formula: (wherein Z 1 is NR 4 (R 4 is hydrogen, optionally substituted lower alkyl etc.), O or CH 2 ; Z 2 is optionally substituted lower alkylene or optionally substituted lower alkenylene, each may be intervened by a heteroatom group selected from group consisting O, S, SO, SO 2 , NR 5 (R 5 is selected independently from the same substituent group of R 4 )—N═ and ═N—; R 1 is hydrogen or lower alkyl; X is a single bond, a heteroatom group selected from O, S, SO, SO 2 and NH, or lower alkylene or lower alkenylene each may be intervened by the heteroatom group; R 2 is optionally substituted aryl; R 3 is hydrogen, halogen, hydroxy, optionally substituted alkyl group etc.)

  [目的]提供一种具有抗病毒活性，特别是HIV整合酶抑制活性的新化合物和一种药剂，特别是抗HIV药剂。 [解决方法]一种由以下公式表示的化合物： （其中Z1为NR4（R4为氢，可选择性取代的低碳基等），O或CH2； Z2为可选择性取代的低位撑链或可选择性取代的低位烯链，每个可以由从O，S，SO，SO2，NR5（R5为独立选择自R4的相同取代基团）-N═和═N-组成的杂原子基团隔开； R1为氢或低碳基； X为单键，从O，S，SO，SO2和NH中选择的杂原子基团，或者可选择性被杂原子基团隔开的低位撑链或低位烯链； R2为可选择性取代的芳基； R3为氢，卤素，羟基，可选择性取代的烷基等。
• Bicyclic carbamoylpyridone derivative having HIV integrase inhibitory activity
  申请人：Shionogi & Co., Ltd.

  公开号：US07858788B2

  公开（公告）日：2010-12-28

  Is to provide a novel compound having an anti-viral activity, particularly a HIV integrase inhibitory activity, and an agent, particularly an anti-HIV agent. A compound represented by the formula: (wherein Z1 is NR4 (R4 is hydrogen, optionally substituted lower alkyl etc.), O or CH2; Z2 is optionally substituted lower alkylene or optionally substituted lower alkenylene, each may be intervened by a heteroatom group selected from group consisting O, S, SO, SO2, NR5 (R5 is selected independently from the same substituent group of R4) —N═ and ═N—; R1 is hydrogen or lower alkyl; X is a single bond, a heteroatom group selected from O, S, SO, SO2 and NH, or lower alkylene or lower alkenylene each may be intervened by the heteroatom group; R2 is optionally substituted aryl; R3 is hydrogen, halogen, hydroxy, optionally substituted alkyl group etc.)

  提供一种具有抗病毒活性，特别是HIV整合酶抑制活性的新型化合物和制剂，特别是抗HIV制剂。该化合物的表示式为：（其中Z1为NR4（R4为氢，可选取取代基较低的烷基等），O或CH2; Z2为可选取取代基较低的亚烷基或可选取取代基较低的烯基，每个均可由从O、S、SO、SO2、NR5（R5从与R4相同的取代基群中独立选择）-N═和═N-组成的杂原子基团中介；R1为氢或较低的烷基；X为单键，从O、S、SO、SO2和NH中选择的杂原子基团，或可选取取代基较低的亚烷基或可选取取代基较低的烯基，每个均可由杂原子基团中介；R2为可选取取代基的芳基；R3为氢，卤素，羟基，可选取取代基的烷基等。
• Polycyclic carbamoylpyridone derivative having HIV integrase inhibitory activity
  申请人：Shionogi & Co., Ltd.

  公开号：US08188271B2

  公开（公告）日：2012-05-29

  Is to provide a novel compound having an anti-viral activity, particularly a HIV integrase inhibitory activity, and a pharmaceutical composition, particularly an anti-HIV agent. (wherein R1 is hydrogen or lower alkyl; X is lower alkylene etc.; R2 is optionally substituted aryl; R3 is hydrogen, halogen, hydroxy, optionally substituted lower alkyl etc.; R4 is hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl, optionally substituted aryl, optionally substituted aryl lower alkyl, optionally substituted heterocyclic group, optionally substituted heterocyclic lower alkyl etc.; A broken line indicates the presence or absence of a bond; B1 and B2 are such that any one of them is CR20R21, and the other is NR22 and, in this case, there is no broken line. When B2 is NR22, R4 and R22 may be connected together to form an optionally substituted heterocycle; When B2 is CHR21, R4 and R21 may be connected together to form an optionally substituted heterocycle. Alternatively, B1 and B2 are independently C, CR23 or N and, in this case, B1 and B2 may be taken together to form a heterocycle. R20, R21, R22 and R23 are independently hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkyl lower alkyl etc.)

  提供一种具有抗病毒活性的新化合物，特别是具有HIV整合酶抑制活性的化合物，以及一种制药组合物，特别是一种抗HIV药物。（其中R1为氢或较低的烷基；X为较低的烷基等；R2为可选取代的芳基；R3为氢、卤素、羟基、可选取代的较低烷基等；R4为氢、可选取代的较低烷基、可选取代的环烷基、可选取代的环烷基较低烷基、可选取代的芳基、可选取代的芳基较低烷基、可选取代的杂环基、可选取代的杂环较低烷基等；破折线表示键的存在或不存在；B1和B2是这样的，其中任意一个是CR20R21，另一个是NR22，此时没有破折线。当B2为NR22时，R4和R22可以连接在一起形成可选取代的杂环；当B2为CHR21时，R4和R21可以连接在一起形成可选取代的杂环。或者，B1和B2独立地为C、CR23或N，此时B1和B2可以结合形成一个杂环。R20、R21、R22和R23独立地为氢、可选取代的较低烷基、可选取代的环烷基、可选取代的环烷基较低烷基等。）