5-(n-butanoyl)-6-methyl-2(1H)-pyridinone | 88302-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(n-butanoyl)-6-methyl-2(1H)-pyridinone
• 英文别名: 5-Butanoyl-6-methylpyridin-2(1H)-one；5-butanoyl-6-methyl-1H-pyridin-2-one
• CAS: 88302-14-1
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: MSXMPMNVVDJBHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(n-butanoyl)-6-methyl-2(1H)-pyridinone 在 N-甲基吡咯烷酮 、 乙酸铵 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氨 、 三氯氧磷 作用下， 以 四氯化碳 为溶剂， 反应 57.0h， 生成 8-propylthiazolo<4,5-b><1,6>naphthyridine-2(3H)-thione
  参考文献：
  名称：

  Novel and Potent Adenosine 3',5'-Cyclic Phosphate Phosphodiesterase III Inhibitors: Thiazolo[4,5-b][1,6]naphthyridin-2-ones

  摘要：

  The transformation of 3-bromo-1,6-naphthyridin-2(1H)-ones 8 to thiazolo[4,5-b][1,6]naphthyridin-2(1H)-ones 12 resulted in a 2-9-fold increase in cAMP phosphodiesterase (PDE) III inhibitory potency. Unlike the secondary binding sites on the cAMP PDE III isozyme which interact with the methyl group of milrinone (2) and CI-930 (4), the site which interacts with the 5-substituents of 1,6-naphthyridin-2(1H)-ones and the 8-substituents of thiazolo[4,5-b][1,6]-naphthyridin-2(1H)-ones 12 is able to accommodate a diverse group of substituents which have different steric and electronic requirements.

  DOI：

  10.1021/jm00014a007
• 作为产物：
  描述：

  庚烷-2,4-二酮 在 乙酸铵 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.5h， 生成 5-(n-butanoyl)-6-methyl-2(1H)-pyridinone
  参考文献：
  名称：

  Singh, Baldev; Lesher, George Y., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2085 - 2091

  摘要：

  DOI：

文献信息

• 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。
• 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为低碳基，R'为氢或甲基，R"为氢或低碳基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可作为心力衰竭药物（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，可作为心力衰竭药物（II，Q'为氢）和/或其中间体（II，Q'为氰基或氢）。显示了制备I和II式化合物的过程。
• 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their
  申请人：Sterling Drug Inc.

  公开号：US04524149A1

  公开（公告）日：1985-06-18

  4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

  4-R.sub.2 -5-(低碳酰基)-6-(低烷基)-2(1H)-吡啶酮(I)是一种有益于心脏的强心剂，其中R.sub.2为氢或甲基，通过将2-(低碳酰基)-1-(低烷基)乙烯胺(II)分别与低烷基2-丙炔酸酯或2-丁炔酸酯反应或通过水解4-R.sub.2-5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酰腈(III)(其中Q为CN)或相应的4-R.sub.2-5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酰胺以产生相应的5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酸，并脱羧化所述取代烟酸酸以产生I。还揭示和声明了3-Q-4-R.sub.2-5-(低碳酰基)-6-(低烷基)-2(1H)-吡啶酮的强心剂用途，其中Q为氢或氰，R.sub.2为氢或甲基(III)。还显示和声明了甲基4-乙酰基-5-氨基-2,4-己二烯酸酯或其酸盐加成物，可用作中间体或强心剂。
• 3-Substituted-5-alkyl-1,6-naphthyridin-2(1H)-ones, cardiotonic use and
  申请人：Sterling Drug Inc.

  公开号：US04559347A1

  公开（公告）日：1985-12-17

  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-2(1H)-酮(I)或其盐，其中R是低碳基，R'是氢或甲基，R"是氢或低碳基，Q是氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可用作心力衰竭药物（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'是氢或氰基，可用作心力衰竭药物（II，Q'为氢）和/或其中间体（II，Q'为氰基或氢）。显示了制备式I和式II化合物的方法。
• Alkanoylpyridinones useful as cardiotonics and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0089022A2

  公开（公告）日：1983-09-21

  3-Q-4-R2-5-(Lower-alkanoyl)-6-(lower-alkyt)-2(1H)-pyridinones (I), useful as cardiotonics, where Q is hydrogen or cyano, R2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R2-5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2- oxonicotinonitrile or corresponding 4-R2-5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotonic acid and decarboxylating said substituted nicotinic acid to produce I. Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiontonic.

  3-Q-4-R2-5-(低级烷酰基)-6-(低级烷基)-2(1H)-吡啶酮 (I)，可用作强心剂，其中 Q 为氢或氰基，R2 为氢或甲基、分别通过 2-(低级烷酰基)-1-(低级烷基)乙烯胺 (II) 与低级烷基 2-丙炔酸酯或 2-丁炔酸酯反应，或通过水解 4-R2-5-(低级烷酰基)-6-(低级烷基)-1、或相应的 4-R2-5-(低级烷酰基)-6-(低级烷基)-1,2-二氢-2-氧代烟酰胺水解生成相应的 5-(低级烷酰基)-6-(低级烷基)-1,2-二氢-2-氧代烟酸，并将所述取代的烟酸脱羧生成 I。图中还显示并要求得到 4-乙酰基-5-氨基-2,4-己二烯酸甲酯或其酸加成盐，可用作中间体或心酮酸。