5-ethyl-4-hydroxy-6-methylpyridin-2(1H)-one | 172469-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-ethyl-4-hydroxy-6-methylpyridin-2(1H)-one
• 英文别名: 5-ethyl-6-methyl-4-hydroxy-2(1H)-pyridinone；5-ethyl-4-hydroxy-6-methyl-1H-pyridin-2-one；5-Ethyl-4-hydroxy-6-methyl-2(1H)-pyridinone
• CAS: 172469-75-9
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: SSTDHRRYEGDLAD-UHFFFAOYSA-N

物化性质

• 熔点：
  330 °C (decomp)
• 沸点：
  313.6±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-ethyl-4-hydroxy-6-methylpyridin-2(1H)-one 在 苄基三乙基氯化铵 、 硝酸 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 1.87h， 生成 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：

  乙基(2Z)-3-氨基-2-乙基-2-丁烯酸酯 在 氢氧化钾 、 乙醇 、 水 、 sodium ethanolate 作用下， 生成 5-ethyl-4-hydroxy-6-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Wibaut; Kooyman, Recueil des Travaux Chimiques des Pays-Bas, 1944, vol. 63, p. 231,236

  摘要：

  DOI：

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。
• Pyridinone and pyridinethione derivatives having hiv inhibiting properties
  申请人：——

  公开号：US20040229847A1

  公开（公告）日：2004-11-18

  The present invention is concerned among others with compounds of formula (I), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C 1-6 alkyl or C 2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R 1 is aryl; R 2 is selected from formyl; C 1-6 alkyloxycarbonylalkyl; Het 2 ; Het 2 C 1-6 alkyl, C 1-6 alkylthio; C 1-6 alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R 3 is selected from formyl; C 1-6 alkyl optionally substituted with one or two C 1-6 alkyloxy; R 1 is hydrogen, with HTV inhibiting properties. 1

  本发明涉及式(I)的化合物，其N-氧化物，药学上可接受的加成盐，季铵盐和立体化学异构体形式，其中Q是卤素，C1-6烷基或C2-6烯基; X为(a-2)，其中q和r为O，Z为O，S或SO; R1为芳基; R2选自甲酰基; C1-6烷氧羰基烷基; Het2; Het2C1-6烷基，C1-6烷基硫醚; C1-6烷基，可选用一个或两个取代基，独立地选自羟基和卤素; R3选自甲酰基; C1-6烷基，可选用一个或两个C1-6烷氧基; R1为氢，具有HTV抑制性能。
• HETEROARYL INHIBITORS OF PDE4
  申请人：Tetra Discovery Partners, LLC

  公开号：US20150119362A1

  公开（公告）日：2015-04-30

  The present invention relates to compounds and methods useful as inhibitors of phosphodiesterase 4 (PDE4) for the treatment or prevention of disease.

  本发明涉及化合物和方法，用于作为磷酸二酯酶4（PDE4）的抑制剂，用于治疗或预防疾病。
• Heteroaryl inhibitors of PDE4
  申请人：Tetra Discovery Partners, LLC

  公开号：US09221843B2

  公开（公告）日：2015-12-29

  The present invention relates to compounds and methods useful as inhibitors of phosphodiesterase 4 (PDE4) for the treatment or prevention of disease.

  本发明涉及化合物和方法，用于作为磷酸二酯酶4（PDE4）的抑制剂，用于治疗或预防疾病。