2-chloro-N-(naphthalen-1-yl)-5-nitropyrimidin-4-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-N-(naphthalen-1-yl)-5-nitropyrimidin-4-amine
• 英文别名: 2-chloro-N-naphthalen-1-yl-5-nitropyrimidin-4-amine
• 化学式: C₁₄H₉ClN₄O₂
• 分子量: 300.704
• InChiKey: KFWSGDFIHXWNDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(naphthalen-1-yl)-5-nitropyrimidin-4-amine 在 potassium carbonate 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 14.0h， 生成 3-chloro-4-(2-((2-chloro-9-(naphthalen-1-yl)-9H-purin-8-yl)thio)propanamido)benzamide
  参考文献：
  名称：

  Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach

  摘要：

  By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1 (IIIB) with EC50 in the range of 0.78-4.46 mu M. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50 = 0.78 mu M, SI = 24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50 = 5.64 mu M) and double mutant strain RES056 (EC50 = 22.24 mu M). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.07.041
• 作为产物：
  描述：

  4-溴-1-萘胺 、 2,4-二氯-5 硝基嘧啶 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 2-chloro-N-(naphthalen-1-yl)-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach

  摘要：

  By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1 (IIIB) with EC50 in the range of 0.78-4.46 mu M. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50 = 0.78 mu M, SI = 24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50 = 5.64 mu M) and double mutant strain RES056 (EC50 = 22.24 mu M). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.07.041

文献信息

• Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach
  作者：Xueyi Lu、Xiao Li、Jiapei Yang、Boshi Huang、Dongwei Kang、Fabao Zhao、Zhongxia Zhou、Erik De Clercq、Dirk Daelemans、Christophe Pannecouque、Peng Zhan、Xinyong Liu

  DOI：10.1016/j.bmc.2016.07.041

  日期：2016.9

  By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1 (IIIB) with EC50 in the range of 0.78-4.46 mu M. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50 = 0.78 mu M, SI = 24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50 = 5.64 mu M) and double mutant strain RES056 (EC50 = 22.24 mu M). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization. (C) 2016 Elsevier Ltd. All rights reserved.