methyl 4-((4-(5-(4-cyano-2,6-dimethylphenoxy)-2-nitrophenylamino)piperidin-1-yl)methyl)benzoate | 1531589-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl 4-((4-(5-(4-cyano-2,6-dimethylphenoxy)-2-nitrophenylamino)piperidin-1-yl)methyl)benzoate
• 英文别名: Methyl 4-[[4-[5-(4-cyano-2,6-dimethyl-phenoxy)-2-nitro-anilino]-1-piperidyl]methyl]benzoate；methyl 4-[[4-[5-(4-cyano-2,6-dimethylphenoxy)-2-nitroanilino]piperidin-1-yl]methyl]benzoate
• CAS: 1531589-89-5
• 化学式: C₂₉H₃₀N₄O₅
• 分子量: 514.581
• InChiKey: CFWFYZURJXETHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氯-2-氟硝基苯 在 四丁基溴化铵 、 sodium carbonate 、 potassium carbonate 、 三氟乙酸 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 methyl 4-((4-(5-(4-cyano-2,6-dimethylphenoxy)-2-nitrophenylamino)piperidin-1-yl)methyl)benzoate
  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

文献信息

• Design, synthesis and preliminary SAR studies of novel N-arylmethyl substituted piperidine-linked aniline derivatives as potent HIV-1 NNRTIs
  作者：Lingzi Zhang、Peng Zhan、Xuwang Chen、Zhenyu Li、Zhoumeng Xie、Tong Zhao、Huiqing Liu、Erik De Clercq、Christophe Pannecouque、Jan Balzarini、Xinyong Liu

  DOI：10.1016/j.bmc.2013.10.033

  日期：2014.1

  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.