5-乙酰基-6-甲基-2(1H)-吡啶酮 | 5220-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-乙酰基-6-甲基-2(1H)-吡啶酮
• 英文名称: 5-acetyl-6-methyl-2(1H)-pyridinone
• 英文别名: 5-acetyl-6-methylpyridin-2(1H)-one；5-acetyl-6-methyl-1H-pyridin-2-one
• CAS: 5220-65-5
• 化学式: C₈H₉NO₂
• mdl: MFCD26517502
• 分子量: 151.165
• InChiKey: JTLWXFRVOPSNEH-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205°

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-乙酰基-6-甲基-2(1H)-吡啶酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 13.0h， 生成 5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193
• 作为产物：
  描述：

  3-dimethylaminomethylenepentane-2,4-dione 在 盐酸 、 铜 作用下， 以 喹啉 、 乙醇 为溶剂， 反应 21.0h， 生成 5-乙酰基-6-甲基-2(1H)-吡啶酮
  参考文献：
  名称：

  Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1503 - 1509

  摘要：

  DOI：

文献信息

• Imidazo(1,2-a)pyridines. I. Synthesis and Inotropic Activity of New 5-Imidazo(1,2-a)pyridinyl-2(1H)-pyridinone Derivatives.
  作者：Motosuke YAMANAKA、Kazutoshi MIYAKE、Shinji SUDA、Hideto OHHARA、Toshiaki OGAWA

  DOI：10.1248/cpb.39.1556

  日期：——

  A series of 1, 2-dihydro-5-imidazo[1, 2-α]pyridinyl-2(1H)-pyridonones was synthesized and evaluated for positive inotropic activity. 1, 2-Dihydro-5-imidazo[1, 2-α]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1, 2-α]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increse in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1, 2-dihydro-5-(6-fluoroimidazo[1, 2-α]pyridin-2-yl)-6-methyl-2(1H)-pyridinone (3u) was the most potent (i.v. ED50 11 μg/kg) in this series. E-1020 is presently under development for the treatment of congestive heart failure.

  合成了一系列1,2-二氢-5-咪唑[1,2-α]吡啶基-2(1H)-吡啶酮，并评估了它们的正性变力活性。1,2-二氢-5-咪唑[1,2-α]吡啶-6-基-6-甲基-2-氧-3-吡啶腈(11a)盐酸盐一水合物(E-1020)被发现是一种强效且选择性的磷酸二酯酶III抑制剂，以及一种长效、强效、口服活性正性变力剂。还制备了额外的咪唑[1,2-α]吡啶-2-基(3a)、-3-基(16)、-7-基(20)和-8-基(24a)化合物。将吡啶取代从2位改变到6位，静脉注射强心效力(ED50)从52增加到23 μg/kg，增加了2倍，而在3-、7-或8位取代则降低了效力。在2位异构体中，引入卤素基团增强了活性，3-氯-1,2-二氢-5-(6-氟咪唑[1,2-α]吡啶-2-基)-6-甲基-2(1H)吡啶酮(3u)是该系列中最强效的(静脉ED50 11 μg/kg)。E-1020目前正在开发用于治疗充血性心力衰竭。
• [EN] NEW ACETYL COENZYME A CARBOXYLASE (ACC) INHIBITORS AND USES IN TREATMENTS OF OBESITY AND DIABETES MELLITUS - 087<br/>[FR] NOUVEAUX INHIBITEURS DE L'ACÉTYL COENZYME A CARBOXYLASE (ACC) ET UTILISATIONS DANS LE TRAITEMENT DE L'OBÉSITÉ ET DU DIABÈTE SUCRÉ - 087
  申请人：ASTRAZENECA AB

  公开号：WO2009082346A1

  公开（公告）日：2009-07-02

  The present invention relates to Acetyl Coenzyme A Carboxylase (ACC) inhibitors according to formula (I), or an enantiomer thereof, or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, E, L, Z and n are as defined herein, to processes for preparing such compounds, to pharmaceutical compositions containing them, to the use of such inhibitors and to methods for th eir therapeutic use, particularly in the treatments of obesity and diabetes mellitus.

  本发明涉及根据式（I）的乙酰辅酶A羧化酶（ACC）抑制剂，或其对映体，或其药用可接受的盐，其中R1、R2、R3、R4、R5、E、L、Z和n的定义如本文所述，以及制备此类化合物的方法，含有它们的药物组合物，使用这种抑制剂以及用于它们的治疗用途的方法，特别是用于肥胖和糖尿病的治疗。
• Certain 2-(1H)-pyridinones cardiotonic compositions containing same and
  申请人：Sterling Drug Inc.

  公开号：US04415580A1

  公开（公告）日：1983-11-15

  1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q"-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.

  1-R"-3-Q-4-R'-5-R-1,6-萘啶并[2(1H)-酮]（I）或其盐，其中R为低碳烷基，R'为氢或甲基，R"为氢或低碳烷基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可用作强心药剂（I，Q为氢、羟基、氨基、氰基或氨基甲酰基）和/或其中间体（I，Q为羧基、氨基甲酰基、氢、氨基、氰基或氨基甲酰基）。还显示了3-Q"-4-R'-5-(RCO)-6-[2-(二低碳烷基氨基)乙烯基]-2(1H)-吡啶酮（II）或其盐，其中R和R'如上所述，Q'为氢或氰基，可用作强心剂（II，Q'为氢）和/或其中间体（II，Q'为氰基或氢）。显示了制备式I和II化合物的方法。
• 5-Alkyl-1,6-naphthyridin-2(1H)-ones and cardiotonic use thereof
  申请人：Sterling Drug Inc.

  公开号：US04517190A1

  公开（公告）日：1985-05-14

  1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q'-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.

  1-R"-3-Q-4-R'-5-R-1,6-萘啉并吡啶-2(1H)-酮(I)或其盐，其中R为较低烷基，R'为氢或甲基，R"为氢或较低烷基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可用作强心药剂(I，Q为氢、羟基、氨基、氰基或氨基甲酰基)和/或其中间体(I，Q为羧基、氨基甲酰基、氢、氨基、氰基或氨基甲酰基)。还显示了3-Q'-4-R'-5-(RCO)-6-[2-(二次较低烷基氨基)乙烯基]-2(1H)-吡啶酮(II)或其盐，其中R和R'如上所述，Q'为氢或氰基，可用作强心剂(II，Q'为氢)和/或中间体(II，Q'为氰基或氢)。显示了制备式I和II化合物的方法。
• Novel alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04732982A1

  公开（公告）日：1988-03-22

  This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.

  这项发明涉及5-酰基-2（1H）-吡啶酮的烷氧基亚胺醚衍生物，以及它们作为心脏强效药物在治疗心力衰竭方面的用途，以及用于其制备的工艺。