[(3,5-Dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methyl-4-pyridyl]methyl] acetate | 248248-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3,5-Dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methyl-4-pyridyl]methyl] acetate
• 英文别名: [(3,5-dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methylpyridin-4-yl]methyl] acetate
• CAS: 248248-99-9
• 化学式: C₂₅H₃₄N₂O₄
• 分子量: 426.556
• InChiKey: NILMGJQQKLECIG-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  532.9±50.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3,5-Dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methyl-4-pyridyl]methyl] acetate 在 30percent Pd/C 盐酸 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 27.5h， 生成 3-amino-4-(3,5-dimethylbenzyl)-5-ethyl-6-methylpyridin-2(1H)-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：

  3,5-二甲基苯甲醛 在 吡啶 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 97.0h， 生成 [(3,5-Dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methyl-4-pyridyl]methyl] acetate
  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

• 3-(Amino-or aminoalkyl) pyridinone derivatives and their use for the treatment of HIV related diseases
  申请人：Centre National De La Recherche Scient.

  公开号：US20030125340A1

  公开（公告）日：2003-07-03

  3-(amino- or aminoalkyl) pyridinone derivatives having the formula (1) 1 wherein Q, X, Y, and R 3 -R 6 are as defined, which derivatives are useful for the treatment of HIV related diseases.

  具有以下式子（1）的3-（氨基或氨基烷基）吡啶酮衍生物，其中Q、X、Y和R3-R6如定义，这些衍生物对于治疗与HIV相关的疾病是有用的。
• 3-(AMINO- OR AMINOALKYL)PYRIDINONE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF HIV RELATED DISEASES
  申请人：CENTRE NATIONAL DELA RECHERCHE SCIENTIFIQUE

  公开号：EP1073637A1

  公开（公告）日：2001-02-07
• US6451822B1
  申请人：——

  公开号：US6451822B1

  公开（公告）日：2002-09-17
• US6683079B2
  申请人：——

  公开号：US6683079B2

  公开（公告）日：2004-01-27
• [EN] 3-(AMINO- OR AMINOALKYL)PYRIDINONE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF HIV RELATED DISEASES<br/>[FR] DERIVES DE 3-(AMINO- OU AMINOALKYL)PYRIDINONE ET UTILISATION DE CEUX-CI DANS LE TRAITEMENT DE PATHOLOGIES ASSOCIEES AU VIH
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：WO1999055676A1

  公开（公告）日：1999-11-04

  (EN) The present invention is concerned with 3-(amino- or aminoalkyl)pyridinone derivatives which inhibit the reverse transcriptase of the Human Immunodeficiency Virus (HIV). It relates moreover to the use of such compounds for treating HIV-related diseases. Furthermore it relates to a process for the preparation of these compounds.(FR) L'invention concerne les dérivés de 3-(amino- ou aminoalkyl)pyridinone qui inhibent la transcriptase inverse du virus de l'immunodéficience humaine (VIH). L'invention concerne également l'utilisation de ces composés pour traiter les pathologies associées au VIH ainsi qu'un procédé de préparation de ces composés.