N-[4-[1-(3,5-dimethylphenyl)-1-hydroxy-ethyl]-5-ethyl-2-methoxy-6-methyl-3-pyridyl]-2,2-dimethyl-propanamide | 311319-94-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[4-[1-(3,5-dimethylphenyl)-1-hydroxy-ethyl]-5-ethyl-2-methoxy-6-methyl-3-pyridyl]-2,2-dimethyl-propanamide
• 英文别名: N-[4-[1-(3,5-dimethylphenyl)-1-hydroxyethyl]-5-ethyl-2-methoxy-6-methylpyridin-3-yl]-2,2-dimethylpropanamide
• CAS: 311319-94-5
• 化学式: C₂₄H₃₄N₂O₃
• 分子量: 398.546
• InChiKey: SPNJGNNPWDQKEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4-[1-(3,5-dimethylphenyl)-1-hydroxy-ethyl]-5-ethyl-2-methoxy-6-methyl-3-pyridyl]-2,2-dimethyl-propanamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 21.0h， 以66%的产率得到N-[4-[1-(3,5-dimethylphenyl)-1-hydroxy-ethyl]-5-ethyl-6-methyl-2-oxo-1H-pyridin-3-yl]-2,2-dimethyl-propanamide
  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：

  3,5-二甲基苯甲醛 在 manganese(IV) oxide 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 31.0h， 生成 N-[4-[1-(3,5-dimethylphenyl)-1-hydroxy-ethyl]-5-ethyl-2-methoxy-6-methyl-3-pyridyl]-2,2-dimethyl-propanamide
  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.