N2-mesityl-N4-methyl-N6-(1-Boc-piperidin-4-yl)-1,3,5-triazine-2,4,6-triamine | 1352804-08-0

• 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: N2-mesityl-N4-methyl-N6-(1-Boc-piperidin-4-yl)-1,3,5-triazine-2,4,6-triamine
• 英文别名: Tert-butyl 4-[[4-(methylamino)-6-(2,4,6-trimethylanilino)-1,3,5-triazin-2-yl]amino]piperidine-1-carboxylate
• CAS: 1352804-08-0
• 化学式: C₂₃H₃₅N₇O₂
• 分子量: 441.577
• InChiKey: VZDPITSDIGHZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N2-mesityl-N4-methyl-N6-(1-Boc-piperidin-4-yl)-1,3,5-triazine-2,4,6-triamine 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N₂-mesityl-N₄-(1-(4-methoxybenzyl)piperidin-4-yl)-N₆-methyl-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of piperidine-substituted triazine derivatives have been synthesized and evaluated for anti-HIV activities in MT-4 cells. Most compounds displayed extremely promising activity against wildtype HIV-1 with EC50 values in low nanomolar concentration, better than that of Nevirapine, Delavirdine, Zidovudine and Dideoxycitidine, and higher potency towards the resistant mutant strain K103N/Y181C than that of Nevirapine and Delavirdine. Selected compounds were also assayed against reverse transcriptase with lower IC50 values than that of Nevirapine. The structure-activity relationship (SAR) of these novel structural congeners was also discussed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.019
• 作为产物：
  描述：

  4,6-dichloro-N-mesityl-1,3,5-triazin-2-amine 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 N2-mesityl-N4-methyl-N6-(1-Boc-piperidin-4-yl)-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of piperidine-linked amino-triazine derivatives were designed, synthesized and evaluated for in vitro anti-HIV activity as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. Screening results indicated that most compounds showed excellent activity against wild-type HIV-1 with EC50 values in low nanomolar concentration range (especially compound 6b3, EC50 = 4.61 nM, SI = 5945) and high activity against K103N/Y181C resistant mutant strain of HIV-1 with EC50 values in low micromolar concentration range. In addition, preliminary structure-activity relationship and molecular modeling of these new analogs were detailed in this manuscript. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.030

文献信息

• Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Xuwang Chen、Peng Zhan、Christophe Pannecouque、Jan Balzarini、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.ejmech.2012.02.019

  日期：2012.5

  A novel series of piperidine-substituted triazine derivatives have been synthesized and evaluated for anti-HIV activities in MT-4 cells. Most compounds displayed extremely promising activity against wildtype HIV-1 with EC50 values in low nanomolar concentration, better than that of Nevirapine, Delavirdine, Zidovudine and Dideoxycitidine, and higher potency towards the resistant mutant strain K103N/Y181C than that of Nevirapine and Delavirdine. Selected compounds were also assayed against reverse transcriptase with lower IC50 values than that of Nevirapine. The structure-activity relationship (SAR) of these novel structural congeners was also discussed. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors
  作者：Xuwang Chen、Peng Zhan、Xin Liu、Ziheng Cheng、Caicai Meng、Siyuan Shao、Christophe Pannecouque、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.bmc.2012.04.030

  日期：2012.6

  A novel series of piperidine-linked amino-triazine derivatives were designed, synthesized and evaluated for in vitro anti-HIV activity as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. Screening results indicated that most compounds showed excellent activity against wild-type HIV-1 with EC50 values in low nanomolar concentration range (especially compound 6b3, EC50 = 4.61 nM, SI = 5945) and high activity against K103N/Y181C resistant mutant strain of HIV-1 with EC50 values in low micromolar concentration range. In addition, preliminary structure-activity relationship and molecular modeling of these new analogs were detailed in this manuscript. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.