4-((4-benzoyl-5-methylpyrimidin-2-yl)amino)benzonitrile | 1232683-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((4-benzoyl-5-methylpyrimidin-2-yl)amino)benzonitrile
• CAS: 1232683-97-4
• 化学式: C₁₉H₁₄N₄O
• 分子量: 314.346
• InChiKey: COUTZRVCTXCDBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((4-benzoyl-5-methylpyrimidin-2-yl)amino)benzonitrile 在 sodium cyanoborohydride 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 4-((4-((cyclopropylamino)(phenyl)methyl)-5-methylpyrimidin-2-yl)amino)benzonitrile
  参考文献：
  名称：

  Design and synthesis of a new series of cyclopropylamino-linking diarylpyrimidines as HIV non-nucleoside reverse transcriptase inhibitors

  摘要：

  A new series of 29 diarylpyrimidine analogues featuring a cyclopropylamino group between the pyrimidine scaffold and the aryl wing have been synthesized. All of the new compounds have been characterized by spectra analysis. The target molecules were evaluated for their in vitro anti-HIV activity with FDA-approved drugs as references. Some of the compounds exhibited moderate to potent activities against wild-type HIV-1. The compound 4-((4-((cyclopropylamino)(2,5-difluorophenyl)methyl)pyrimidin-2-yl)amino)benzonitrile (1e) displayed potent anti-HIV-1 activity against WT HIV-1 with an IC50 of 0.099 μM and a selectivity index of 2302. The preliminary structure-activity relationship (SAR) of this new series of compounds was also investigated.

  DOI：

  10.1016/j.ejps.2014.06.003
• 作为产物：
  描述：

  4-[(4-methyl-6-oxo-1H-pyrimidin-2-yl)amino]benzonitrile 在 氧气 、 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 生成 4-((4-benzoyl-5-methylpyrimidin-2-yl)amino)benzonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel diarylpyrimidines with hydromethyl linker (CH(OH)-DAPYs) as HIV-1 NNRTIs

  摘要：

  A series of 26 diarylpyrimidines, characterized by the hydroxymethyl linker between the left wing benzene ring and the central pyrimidine, were synthesized and evaluated for in vitro anti-HIV activity. Most of the compounds exhibited moderate to excellent activities against wild-type HIV-1. Among them, compound 10i, bearing a chlorine atom at the C-2 position of left benzene ring, was the best congener and showed potent activity against wild-type HIV-1 with an EC50 value of 0.009 mu M, along with moderate activities against the double RT mutant (K103N + Y181C) HIV-1(IIIB) and HIV-2(ROD) with an EC50 value of 6.2 and 6.0 mu M, respectively. The preliminary structure-activity relationship (SAR) of this new series of compounds was also investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.023