5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone | 88877-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone
• 英文别名: 5-acetyl-6-[2-(dimethylamino)vinyl]-2(1H)-pyridinone；5-acetyl-6-[(E)-2-(dimethylamino)ethenyl]-1H-pyridin-2-one
• CAS: 88877-00-3
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: FLJCJGRJHJFVGA-VOTSOKGWSA-N

物化性质

• 熔点：
  238-240°
• 沸点：
  357.0±42.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

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-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone 在 肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到6-(amino)-5-methyl-1,6-naphthyridin-2(6H)-one
  参考文献：
  名称：

  Novel Synthesis of 1,6-Naphthyridin-2(6H)-ones, Quinolin-2(1H)-ones, and Quino[7,8-f]quinoline-2,9(1H,10H)-dione from Common Precursors

  摘要：

  1,6-萘啶-2(6H)-酮 3、喹啉-2(1H)-酮 5 和喹啉并[7,8-f]喹啉-2,9(1H,10H)-二酮 10 是由 5-酰基-6-[2-（二甲基氨基）乙烯基]吡啶-2(1H)-酮 1 合成的。

  DOI：

  10.1055/s-1992-26090
• 作为产物：
  描述：

  5-乙酰基-6-甲基-2(1H)-吡啶酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 N-甲基乙酰胺 为溶剂， 生成 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone
  参考文献：
  名称：

  5-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and

  摘要：

  4-R'-5-Q-1,6-萘啶并[2(1H)-酮] (I)，其中R'为氢或甲基，Q为羟甲基，1-羟乙基烷酰氧甲基或1-烷酰氧乙基，首先将4-R'-5-乙酰基（或正丙酰基）-6-[2-(二低烷基)氨基]-2(1H)-吡啶酮[III]与羟胺或其盐反应，生成4-R'-5-Q'-1,6-萘啶并[2(1H)-酮]-6-氧化物(II)，其中R'如上所述，Q'为甲基或乙基；然后用脂肪酸酐反应II，生成Q为烷酰氧甲基或1-烷酰氧乙基的I；然后水解所述的烷酰氧甲基或烷酰氧乙基化合物，生成Q为羟甲基或1-羟乙基的I。还显示了II和Q为羟甲基，1-羟乙基或烷酰氧甲基的I的强心作用。

  公开号：

  US04532247A1

文献信息

• 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-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and
  申请人：Sterling Drug Inc.

  公开号：US04532247A1

  公开（公告）日：1985-07-30

  4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl(or n-propanoyl)-6-[2-(di-lower-alkylamino]-2(1H)-pyridinone [III] with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1-alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.

  4-R'-5-Q-1,6-萘啶并[2(1H)-酮] (I)，其中R'为氢或甲基，Q为羟甲基，1-羟乙基烷酰氧甲基或1-烷酰氧乙基，首先将4-R'-5-乙酰基（或正丙酰基）-6-[2-(二低烷基)氨基]-2(1H)-吡啶酮[III]与羟胺或其盐反应，生成4-R'-5-Q'-1,6-萘啶并[2(1H)-酮]-6-氧化物(II)，其中R'如上所述，Q'为甲基或乙基；然后用脂肪酸酐反应II，生成Q为烷酰氧甲基或1-烷酰氧乙基的I；然后水解所述的烷酰氧甲基或烷酰氧乙基化合物，生成Q为羟甲基或1-羟乙基的I。还显示了II和Q为羟甲基，1-羟乙基或烷酰氧甲基的I的强心作用。
• UROTENSIN II RECEPTOR ANTAGONISTS
  申请人：Cook Brian Nicholas

  公开号：US20100121051A1

  公开（公告）日：2010-05-13

  Compounds of the formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W, and Y are as described herein, or a tautomer, prodrug, solvate, or salt thereof. These compounds are useful as inhibitors of Urotensin II and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the interaction of Urotensin II with its receptor, including cardiovascular diseases. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds, and intermediates useful in these processes.

  式（I）的化合物，其中R1、R2、R3、R4、R5、R6、W和Y如本文所述，或其互变异构体、前药、溶剂化物或盐。这些化合物可用作Urotensin II的抑制剂，因此可用于治疗多种通过Urotensin II与其受体的相互作用介导或维持的疾病和障碍，包括心血管疾病。本发明还涉及包含这些化合物的制药组合物，使用这些化合物治疗各种疾病和障碍的方法，制备这些化合物的过程以及在这些过程中有用的中间体。
• 5-Alkyl-1,6-naphthyridin-2(1H)-ones, intermediates, their preparation and their cardiotonic use
  申请人：STERLING DRUG INC.

  公开号：EP0101952A1

  公开（公告）日：1984-03-07

  Naphthyridines of formula (I) , where R is -alkyl, R' is hydrogen or methyl, R" is hydrogen or alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (1, 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 pyridinones of formula II 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.

  式(I)的萘啶类化合物 其中 R 为烷基，R'为氢或甲基，R "为氢或烷基，Q 为氢、羟基、氨基、氰基、氨甲酰、羧基或氨基甲酰，可用作强心剂（1，Q 为氢、羟基、氨基、氰基或氨基甲酰）和/或其中间体（I，Q 为羧基、氨基甲酰、氢、氨基、氰基或氨基甲酰）。图中还显示了式 II 的吡啶酮类化合物 其中 R 和 R'如上，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）。所示为制备式 I 和 II 化合物的工艺。
• 1,6-Naphthyridin derivatives useful as cardiotonics and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0134535A1

  公开（公告）日：1985-03-20

  4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is . hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl (or n-propanoyl)-6-[2-(di- lower-alkylamino]-2(1H)-pyridinone (III) with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1- alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.

  4-R'-5-Q-1,6-萘啶-2(1H)-酮 (I)，其中 R' 是 .氢或甲基，Q 为羟甲基、1-羟乙基烷酰氧基甲基或 1-烷酰氧基乙基、首先将 4-R'-5-乙酰基（或正丙酰基）-6-[2-（二低级烷基氨基）-2(1H)-吡啶酮（III）]与羟胺或其盐反应，生成 4-R'-5-Q'-1,6-萘啶-2(1H)-酮-6-氧化物（II），其中 R'定义如上，Q'为甲基或乙基；再将 II 与烷酸酐反应生成 I，其中 Q 为烷酰氧基甲基或 1-烷酰氧基乙基；然后，水解所述烷酰氧基甲基或-乙基化合物，生成 I，其中 Q 为羟甲基或 1-羟乙基。图中还显示了 II 和 I 的强心剂用途，其中 Q 为羟甲基、1-羟乙基或烷酰氧基甲基。