N-(4-(4-cyano-2,6-dimethylphenoxy)-2-(piperidin-4-ylamino)phenyl)acetamide | 1531589-79-3

• 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: N-(4-(4-cyano-2,6-dimethylphenoxy)-2-(piperidin-4-ylamino)phenyl)acetamide
• 英文别名: N-[4-(4-cyano-2,6-dimethylphenoxy)-2-(piperidin-4-ylamino)phenyl]acetamide
• CAS: 1531589-79-3
• 化学式: C₂₂H₂₆N₄O₂
• 分子量: 378.474
• InChiKey: UQDYSCWZNDRLIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-(4-cyano-2,6-dimethylphenoxy)-2-(piperidin-4-ylamino)phenyl)acetamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到N-(4-(4-cyano-2,6-dimethylphenoxy)-2-(1-(4-sulfamoylbenzyl)piperidin-4-ylamino)phenyl)acetamide
  参考文献：
  名称：

  Design, synthesis and preliminary SAR studies of novel N-arylmethyl substituted piperidine-linked aniline derivatives as potent HIV-1 NNRTIs

  摘要：

  A series of novel N-arylmethyl substituted piperidine-linked aniline derivatives were designed, synthesized and evaluated for their anti-HIV activity in MT-4 cells. All the new compounds showed moderate to potent activities against wild-type (wt) HIV-1 with an EC50 range from 0.022 to 2.1 mu M. Among them, compound 5a6 (EC50 = 0.022 +/- 0.0091 mu M, SI > 10,770) was confirmed to be the most potent and selective inhibitor, which proved more potent than DDI and DLV in a cell-based assay against wt HIV-1, and more efficient than NVP in an RT (reverse transcriptase) assay. Besides, it is worth noting that compound 7a1 retained moderate inhibitory activity (EC50 = 4.8 +/- 0.95 mu M) against the HIV-1 double RT mutant strain (K103N/Y181C). The preliminary structure-activity relationship was discussed and rationalized by molecular simulation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.033
• 作为产物：
  描述：

  tert-butyl 4-(2-acetamido-5-(4-cyano-2,6-dimethylphenoxy)phenylamino)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96.9%的产率得到N-(4-(4-cyano-2,6-dimethylphenoxy)-2-(piperidin-4-ylamino)phenyl)acetamide
  参考文献：
  名称：

  Design, synthesis and preliminary SAR studies of novel N-arylmethyl substituted piperidine-linked aniline derivatives as potent HIV-1 NNRTIs

  摘要：

  A series of novel N-arylmethyl substituted piperidine-linked aniline derivatives were designed, synthesized and evaluated for their anti-HIV activity in MT-4 cells. All the new compounds showed moderate to potent activities against wild-type (wt) HIV-1 with an EC50 range from 0.022 to 2.1 mu M. Among them, compound 5a6 (EC50 = 0.022 +/- 0.0091 mu M, SI > 10,770) was confirmed to be the most potent and selective inhibitor, which proved more potent than DDI and DLV in a cell-based assay against wt HIV-1, and more efficient than NVP in an RT (reverse transcriptase) assay. Besides, it is worth noting that compound 7a1 retained moderate inhibitory activity (EC50 = 4.8 +/- 0.95 mu M) against the HIV-1 double RT mutant strain (K103N/Y181C). The preliminary structure-activity relationship was discussed and rationalized by molecular simulation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.033