2-((4-(4-cyano-2,6-dimethylphenoxy)pyrimidin-2-yl)thio)-N-(o-tolyl)acetamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((4-(4-cyano-2,6-dimethylphenoxy)pyrimidin-2-yl)thio)-N-(o-tolyl)acetamide
• 英文别名: 2-[4-(4-cyano-2,6-dimethyl-phenoxy)pyrimidin-2-yl]sulfanyl-N-(o-tolyl)acetamide；2-[4-(4-cyano-2,6-dimethylphenoxy)pyrimidin-2-yl]sulfanyl-N-(2-methylphenyl)acetamide
• 化学式: C₂₂H₂₀N₄O₂S
• 分子量: 404.492
• InChiKey: BCVFIRXVFBMSOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-((2-chloropyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile 在 potassium tert-butylate 、 硫脲 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-((4-(4-cyano-2,6-dimethylphenoxy)pyrimidin-2-yl)thio)-N-(o-tolyl)acetamide
  参考文献：
  名称：

  Hybrid chemistry. Part 4: Discovery of etravirine–VRX-480773 hybrids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel series of etravirine-VRX-480773 hybrids were designed using structure-guided molecular hybridization strategy and fusing the pharmacophore templates of etravirine and VRX-480773. The anti-HIV-1 activity and cytotoxicity was evaluated in MT-4 cell cultures. The most active hybrid compound in this series, N-(2-chlorophenyl)-2-((4-(4-cyano-2,6-dimethylphenoxy) pyrimidin-2-yl) thio) acetamide 3d (EC50 = 0.24, SI > 1225), was more potent than delavirdine (EC50 = 0.66 mu M, SI > 67) in the anti-HIV-1 in vitro cellular assay. Studies of structure-activity relationships established a correlation between anti-HIV activity and the substitution pattern of the acetanilide group. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.048

文献信息

• Hybrid chemistry. Part 4: Discovery of etravirine–VRX-480773 hybrids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Zheng-Yong Wan、Yuan Tao、Ya-Feng Wang、Tian-Qi Mao、Hong Yin、Fen-Er Chen、Hu-Ri Piao、Erik De Clercq、Dirk Daelemans、Christophe Pannecouque

  DOI：10.1016/j.bmc.2015.06.048

  日期：2015.8

  A novel series of etravirine-VRX-480773 hybrids were designed using structure-guided molecular hybridization strategy and fusing the pharmacophore templates of etravirine and VRX-480773. The anti-HIV-1 activity and cytotoxicity was evaluated in MT-4 cell cultures. The most active hybrid compound in this series, N-(2-chlorophenyl)-2-((4-(4-cyano-2,6-dimethylphenoxy) pyrimidin-2-yl) thio) acetamide 3d (EC50 = 0.24, SI > 1225), was more potent than delavirdine (EC50 = 0.66 mu M, SI > 67) in the anti-HIV-1 in vitro cellular assay. Studies of structure-activity relationships established a correlation between anti-HIV activity and the substitution pattern of the acetanilide group. (C) 2015 Elsevier Ltd. All rights reserved.