5-ethyl-4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone | 163803-33-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-ethyl-4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone
• 英文别名: 5-ethyl-4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one；5-ethyl-4-hydroxy-6-methyl-3-nitro-1H-pyridin-2-one
• CAS: 163803-33-6
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: SCJVPETVSWVJPP-UHFFFAOYSA-N

物化性质

• 沸点：
  319.1±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethyl-4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone 在 苄基三乙基氯化铵 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以34%的产率得到4-chloro-5-ethyl-6-methyl-3-nitropyridin-2(1H)-one
  参考文献：
  名称：

  A New Series of Pyridinone Derivatives as Potent Non-Nucleoside Human Immunodeficiency Virus Type 1 Specific Reverse Transcriptase Inhibitors

  摘要：

  4-(Arylthio)-pyridin-2(1H)-ones variously substituted in their 3-, 5-, and 6-positions have been synthesized as a new series of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-pyridinone hybrid molecules. Biological studies revealed that some of them show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 16 and 7c, the most active ones, inhibit the replication of HIV-1 at 3 and 6 nM, respectively.

  DOI：

  10.1021/jm00023a007
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 盐酸 、 硝酸铵 、 硝酸 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 228.37h， 生成 5-ethyl-4-hydroxy-6-methyl-3-nitro-2(1H)-pyridinone
  参考文献：
  名称：

  A New Series of Pyridinone Derivatives as Potent Non-Nucleoside Human Immunodeficiency Virus Type 1 Specific Reverse Transcriptase Inhibitors

  摘要：

  4-(Arylthio)-pyridin-2(1H)-ones variously substituted in their 3-, 5-, and 6-positions have been synthesized as a new series of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-pyridinone hybrid molecules. Biological studies revealed that some of them show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 16 and 7c, the most active ones, inhibit the replication of HIV-1 at 3 and 6 nM, respectively.

  DOI：

  10.1021/jm00023a007

文献信息

• New Pyridinone Derivatives as Potent HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors
  作者：Kiet Le Van、Christine Cauvin、Stéphane de Walque、Benoît Georges、Sandro Boland、Valérie Martinelli、Dominique Demonté、François Durant、László Hevesi、Carine Van Lint

  DOI：10.1021/jm801438e

  日期：2009.6.25

  Several 5-ethyl-6-methyl-4-cycloalkyloxy-pyridin-2(1H)-ones were synthesized and evaluated for their anti HIV-1 activities against wild-type virus and clinically relevant mutant strains. A racemic mixture (10) with methyl substituents at positions 3 and 5 of the cyclohexyloxy moiety had potent antiviral activity against wild-type HIV-1. Subsequent stereoselective synthesis of a stereoisomer displaying

  合成了几个5-乙基-6-甲基-4-环烷氧基-吡啶-2（1 H）-1 ，并评估了它们对野生型病毒和临床相关突变株的抗HIV-1活性。在环己氧基部分的3和5位带有甲基取代基的外消旋混合物（10）对野生型HIV-1具有有效的抗病毒活性。随后的立体异构体的立体选择性合成显示出两个赤道位置上的甲基均被发现具有最佳的EC 50值。集中在吡啶酮环的位置3上的进一步调节改善了对突变病毒株的抗病毒活性。带有3-乙基（22）或3-异丙基（23）对野生型HIV-1具有最高的活性，并且对几种临床相关的突变株显示出低纳摩尔效价。
• 4-Aryl-thio-pyridin-2(1H)-ones, medicines containing them and their uses
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US06015820A1

  公开（公告）日：2000-01-18

  Compounds of formula (3) in which: R.sub.1 and R.sub.2 independently represent an atom of hydrogen, an aliphatic group or an alkyloxyalkyl group in which the alkyl chains are from C.sub.1 to C.sub.4 or together form an aromatic ring; R.sub.3 represents: an atom of hydrogen, or an NHR.sub.5 group in which R.sub.5 represents an atom of hydrogen or a COR.sub.6 group in which R.sub.6 is an aliphatic or aromatic group, or an NO.sub.2 group or a COOR.sub.7 group in which R.sub.7 is an aliphatic group, R.sub.4 represents a phenyl or heterocyclic group. These compounds can be used in the treatment of illnesses linked to the HIV virus.

  式（3）中的化合物，其中：R.sub.1和R.sub.2分别表示氢原子、脂肪基或烷氧基烷基，其中烷基链为C.sub.1到C.sub.4，或者一起形成芳香环；R.sub.3表示：氢原子，或者NHR.sub.5基团，其中R.sub.5表示氢原子或者COR.sub.6基团，其中R.sub.6是脂肪基或芳香基，或者NO.sub.2基团或COOR.sub.7基团，其中R.sub.7是脂肪基，R.sub.4表示苯基或杂环基团。这些化合物可用于治疗与HIV病毒相关的疾病。
• Intermediates for imidazo[4,5-c]pyridin-4-amines
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05446153A1

  公开（公告）日：1995-08-29

  Imidazo[4,5-c]pyridin-4-amines that induce interferon (.alpha.) biosynthesis in human cells. Also disclosed are pharmaceutical compositions containing such compounds and methods of inducing interferon (.alpha.) biosynthesis involving the use of such compounds.

  本发明涉及诱导人体细胞内干扰素（α）生物合成的咪唑并[4,5-c]吡啶-4-胺类化合物。同时还揭示了含有这些化合物的制药组合物以及使用这些化合物诱导干扰素（α）生物合成的方法。
• Imidazo[4,5-c]pyridin-4-amine intermediates
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05644063A1

  公开（公告）日：1997-07-01

  Imidazo[4,5-c]pyridin-4-amines that induce interferon (.alpha.) biosynthesis in human cells. Also disclosed are pharmaceutical compositions containing such compounds and methods of inducing interferon (.alpha.) biosynthesis involving the use of such compounds.

  本发明涉及诱导人细胞中干扰素（.alpha.）生物合成的咪唑并[4,5-c]吡啶-4-胺化合物。还公开了含有这种化合物的制药组合物和诱导干扰素（.alpha.）生物合成的方法。
• Imidazo[4,5-C]pyridin-4-amines
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05494916A1

  公开（公告）日：1996-02-27

  Imidazo[4,5-c]pyridin-4-amines that induce interferon (.alpha.) biosynthesis in human cells. Also disclosed are pharmaceutical compositions containing such compounds and methods of inducing interferon (.alpha.) biosynthesis involving the use of such compounds.

  本文披露了诱导人类细胞中干扰素(.alpha.)生物合成的咪唑并[4,5-c]吡啶-4-胺化合物。还披露了含有这些化合物的药物组合物以及使用这些化合物诱导干扰素(.alpha.)生物合成的方法。