N-[4-(3,5-Dimethyl-benzyl)-5-ethyl-6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl]-formamide | 311319-90-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[4-(3,5-Dimethyl-benzyl)-5-ethyl-6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl]-formamide
• 英文别名: N-[4-[(3,5-dimethylphenyl)methyl]-5-ethyl-6-methyl-2-oxo-1H-pyridin-3-yl]formamide
• CAS: 311319-90-1
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: XECRNUYXGTTZHB-UHFFFAOYSA-N

物化性质

• 熔点：
  246-247 °C
• 沸点：
  552.1±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[4-(3,5-Dimethyl-benzyl)-5-ethyl-6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl]-formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以57%的产率得到4-(3,5-Dimethyl-benzyl)-5-ethyl-6-methyl-3-methylamino-1H-pyridin-2-one
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 4-Benzyl Pyridinone Derivatives as Potent and Selective Non-Nucleoside Human Immunodeficiency Virus Type 1 Reverse Transcriptase Inhibitors

  摘要：

  Several 4-benzyl analogues of 5-ethyl-6-methyl-4-(phenylthio)pyridin-2(1H)-ones were synthesized and evaluated for their anti-HIV-l activities. Key transformations include metalation at the 4-C-position of 5-ethyl-2-methoxy-6-methyl-3-pivaloylaminopyridine (5) and its coupling with benzyl bromide or benzaldehyde derivatives. Biological studies revealed that some of the new 4-benzylpyridinones show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 14, 19, and 27, which inhibit the replication of HIV-1 in CEM-SS cells, with IC50 values ranging from 0.2 to 6 nM are the most active compounds in this series. Biochemical studies showed that compound 27 strongly inhibited the activity of a recombinant HIV-1 RT. Moreover, the infectivity of isolated HIV-1 particles was severely decreased after exposure to compound 27. Although cross resistance is frequently observed between non-nucleoside reverse transcriptase inhibitors, compound 27 was capable of inhibiting a virus resistant to nevirapine with an IC50 Of 40 nM.

  DOI：

  10.1021/jm0009437
• 作为产物：
  描述：

  3,5-二甲基溴苄 在 盐酸 、 正丁基锂 、 甲酸 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.0h， 生成 N-[4-(3,5-Dimethyl-benzyl)-5-ethyl-6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl]-formamide
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 4-Benzyl Pyridinone Derivatives as Potent and Selective Non-Nucleoside Human Immunodeficiency Virus Type 1 Reverse Transcriptase Inhibitors

  摘要：

  Several 4-benzyl analogues of 5-ethyl-6-methyl-4-(phenylthio)pyridin-2(1H)-ones were synthesized and evaluated for their anti-HIV-l activities. Key transformations include metalation at the 4-C-position of 5-ethyl-2-methoxy-6-methyl-3-pivaloylaminopyridine (5) and its coupling with benzyl bromide or benzaldehyde derivatives. Biological studies revealed that some of the new 4-benzylpyridinones show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 14, 19, and 27, which inhibit the replication of HIV-1 in CEM-SS cells, with IC50 values ranging from 0.2 to 6 nM are the most active compounds in this series. Biochemical studies showed that compound 27 strongly inhibited the activity of a recombinant HIV-1 RT. Moreover, the infectivity of isolated HIV-1 particles was severely decreased after exposure to compound 27. Although cross resistance is frequently observed between non-nucleoside reverse transcriptase inhibitors, compound 27 was capable of inhibiting a virus resistant to nevirapine with an IC50 Of 40 nM.

  DOI：

  10.1021/jm0009437

文献信息

• Synthesis and Antiviral Activity of 4-Benzyl Pyridinone Derivatives as Potent and Selective Non-Nucleoside Human Immunodeficiency Virus Type 1 Reverse Transcriptase Inhibitors
  作者：Valérie Dollé、Chi Hung Nguyen、Michel Legraverend、Anne-Marie Aubertin、André Kirn、Marie Line Andreola、Michel Ventura、Laura Tarrago-Litvak、Emile Bisagni

  DOI：10.1021/jm0009437

  日期：2000.10.1

  Several 4-benzyl analogues of 5-ethyl-6-methyl-4-(phenylthio)pyridin-2(1H)-ones were synthesized and evaluated for their anti-HIV-l activities. Key transformations include metalation at the 4-C-position of 5-ethyl-2-methoxy-6-methyl-3-pivaloylaminopyridine (5) and its coupling with benzyl bromide or benzaldehyde derivatives. Biological studies revealed that some of the new 4-benzylpyridinones show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 14, 19, and 27, which inhibit the replication of HIV-1 in CEM-SS cells, with IC50 values ranging from 0.2 to 6 nM are the most active compounds in this series. Biochemical studies showed that compound 27 strongly inhibited the activity of a recombinant HIV-1 RT. Moreover, the infectivity of isolated HIV-1 particles was severely decreased after exposure to compound 27. Although cross resistance is frequently observed between non-nucleoside reverse transcriptase inhibitors, compound 27 was capable of inhibiting a virus resistant to nevirapine with an IC50 Of 40 nM.