4-(3,5-二甲基苯氧基)-5-乙基-6-甲基-2-氧代-1,2-二氢吡啶-3-羧酸乙酯 | 651778-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(3,5-二甲基苯氧基)-5-乙基-6-甲基-2-氧代-1,2-二氢吡啶-3-羧酸乙酯
• 英文名称: ethyl 4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-2-oxo-1H-pyridine-3-carboxylate
• CAS: 651778-58-4
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: QBESYWRSIUTAKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,5-二甲基苯氧基)-5-乙基-6-甲基-2-氧代-1,2-二氢吡啶-3-羧酸乙酯 在 盐酸 、 硝酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 3-amino-4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-1H-pyridin-2-one
  参考文献：
  名称：

  3-Iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  Building upon the potent anti-HIV-1 activities observed for the 3-dimethylamino-4-benzylpyridinone 2, and the corresponding 4-aryloxypyridinone analogue 3, a concise and efficient route to the 3-iodo-4-aryloxypyridinones 14a-c (IOPY's) was developed. This involved reaction of the 4-hydroxy substituted pyridinone 10 with the requisite dichloroiodobenzene reagent 11. IOPY compound 14c is active at IC50 = 1-45 nM against wild type HIV-1 and a panel of six major simple/double HIV mutant strains. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.045
• 作为产物：
  描述：

  5-乙基-4-羟基-6-甲基-2-氧代-1H-吡啶-3-羧酸乙酯 在 苄基三乙基氯化铵 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-(3,5-二甲基苯氧基)-5-乙基-6-甲基-2-氧代-1,2-二氢吡啶-3-羧酸乙酯
  参考文献：
  名称：

  3-Iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  Building upon the potent anti-HIV-1 activities observed for the 3-dimethylamino-4-benzylpyridinone 2, and the corresponding 4-aryloxypyridinone analogue 3, a concise and efficient route to the 3-iodo-4-aryloxypyridinones 14a-c (IOPY's) was developed. This involved reaction of the 4-hydroxy substituted pyridinone 10 with the requisite dichloroiodobenzene reagent 11. IOPY compound 14c is active at IC50 = 1-45 nM against wild type HIV-1 and a panel of six major simple/double HIV mutant strains. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.045

文献信息

• Structure–activity relationship in the 3-iodo-4-phenoxypyridinone (IOPY) series: The nature of the C-3 substituent on anti-HIV activity
  作者：Abdellah Benjahad、Said Oumouch、Jerôme Guillemont、Elisabeth Pasquier、Dominique Mabire、Koen Andries、Chi Hung Nguyen、David S. Grierson

  DOI：10.1016/j.bmcl.2006.10.082

  日期：2007.2

  As part of a systematic SAR study on the 3-iodo-4-phenoxypyridinone 3 (IOPY) type non-nucleoside reverse transcriptase inhibitors, the analogues 4a-4z bearing different C-3 substituents were synthesized and evaluated for their anti-HIV activity against wild-type HIV-1 and four of the principal HIV mutant strains (K103N, Y181C, Y188L, and 1100L). The results show that the 3-vinyl analogue 4j is the only compound which displays anti-HIV activity comparable to IOPY 3, and in this respect represents a possible back-up to this lead molecule. (c) 2006 Elsevier Ltd. All rights reserved.
• 3-Iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase
  作者：Abdellah Benjahad、Jérôme Guillemont、Koen Andries、Chi Hung Nguyen、David S Grierson

  DOI：10.1016/j.bmcl.2003.09.045

  日期：2003.12

  Building upon the potent anti-HIV-1 activities observed for the 3-dimethylamino-4-benzylpyridinone 2, and the corresponding 4-aryloxypyridinone analogue 3, a concise and efficient route to the 3-iodo-4-aryloxypyridinones 14a-c (IOPY's) was developed. This involved reaction of the 4-hydroxy substituted pyridinone 10 with the requisite dichloroiodobenzene reagent 11. IOPY compound 14c is active at IC50 = 1-45 nM against wild type HIV-1 and a panel of six major simple/double HIV mutant strains. (C) 2003 Elsevier Ltd. All rights reserved.