2-(4-cyanophenylamino)-4-(2-cyanovinyl)(benzoyl)pyrimidine | 1617527-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-cyanophenylamino)-4-(2-cyanovinyl)(benzoyl)pyrimidine
• CAS: 1617527-85-1
• 化学式: C₂₁H₁₃N₅O
• 分子量: 351.367
• InChiKey: PBQGDQYXECIALC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(4-cyanophenylamino)-4-(2-cyanovinyl)(benzoyl)pyrimidine 在 sodium cyanoborohydride 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(4-cyanophenylamino)-4-(4-(2-cyanovinyl)phenyl-N-methylaminomethyl)pyrimidine
  参考文献：
  名称：

  Design and synthesis of a new series of modified CH-diarylpyrimidines as drug-resistant HIV non-nucleoside reverse transcriptase inhibitors

  摘要：

  This article reports the design, synthesis and antiviral evaluation of a new series of non-nucleoside reverse transcriptase inhibitors (NNRTIs). The basic skeleton of these target 18 molecules is diarylpyrimidine featuring a substituted amino group between the pyrimidine scaffold and the aryl wing. All of the new compounds have been characterized by spectra analysis. The entire target molecules were evaluated for their in vitro anti-HIV activity with controlling group of FDA approved drugs. Most of them showed good to potent activities against wild-type (WT) HIV-1 with IC50 values in the range of 0.0175-69.21 mu M. 2-(4-Cyanophenylamino)-4-(2-cyanovinylphenylhydrazonomethyl)pyrimidine (1d) displayed potent anti-HIV-1 activity against WT HIV-1 with a selectivity index (SI) of 106367 and an IC50 value of 1.75 nM, which was 47 fold lower than that of AZT. Compound Id also showed a broad-spectrum inhibitory activity, with an IC50 value of 5.33 mu M and 5.05 mu M against both HIV-1 double-mutated (K103N/Y181C) strain and HIV-2 strain, respectively. The preliminary structure activity relationship (SAR) was also investigated. The binding modes with HIV-1 RT for both the wild type and mutant type have also been discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.059
• 作为产物：
  描述：

  4-[(4-羟基-2-嘧啶基)氨基]苯腈 在 sodium acetate 、 palladium diacetate 、 sodium hydride 、 三(邻甲基苯基)磷 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-(4-cyanophenylamino)-4-(2-cyanovinyl)(benzoyl)pyrimidine
  参考文献：
  名称：

  Design and synthesis of a new series of modified CH-diarylpyrimidines as drug-resistant HIV non-nucleoside reverse transcriptase inhibitors

  摘要：

  This article reports the design, synthesis and antiviral evaluation of a new series of non-nucleoside reverse transcriptase inhibitors (NNRTIs). The basic skeleton of these target 18 molecules is diarylpyrimidine featuring a substituted amino group between the pyrimidine scaffold and the aryl wing. All of the new compounds have been characterized by spectra analysis. The entire target molecules were evaluated for their in vitro anti-HIV activity with controlling group of FDA approved drugs. Most of them showed good to potent activities against wild-type (WT) HIV-1 with IC50 values in the range of 0.0175-69.21 mu M. 2-(4-Cyanophenylamino)-4-(2-cyanovinylphenylhydrazonomethyl)pyrimidine (1d) displayed potent anti-HIV-1 activity against WT HIV-1 with a selectivity index (SI) of 106367 and an IC50 value of 1.75 nM, which was 47 fold lower than that of AZT. Compound Id also showed a broad-spectrum inhibitory activity, with an IC50 value of 5.33 mu M and 5.05 mu M against both HIV-1 double-mutated (K103N/Y181C) strain and HIV-2 strain, respectively. The preliminary structure activity relationship (SAR) was also investigated. The binding modes with HIV-1 RT for both the wild type and mutant type have also been discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.059

文献信息

• Design and synthesis of a new series of cyclopropylamino-linking diarylpyrimidines as HIV non-nucleoside reverse transcriptase inhibitors
  作者：Yang Liu、Ge Meng、Aqun Zheng、Fener Chen、Wenxue Chen、Erik De Clercq、Christophe Pannecouque、Jan Balzarini

  DOI：10.1016/j.ejps.2014.06.003

  日期：2014.10

  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.