N-(3-((2-bromobenzyl)oxy)-4-chlorophenyl)-4-methoxypyrimidin-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3-((2-bromobenzyl)oxy)-4-chlorophenyl)-4-methoxypyrimidin-2-amine
• 英文别名: N-[3-[(2-bromophenyl)methoxy]-4-chloro-phenyl]-4-methoxy-pyrimidin-2-amine；N-[3-[(2-bromophenyl)methoxy]-4-chlorophenyl]-4-methoxypyrimidin-2-amine
• 化学式: C₁₈H₁₅BrClN₃O₂
• 分子量: 420.693
• InChiKey: VINMRSAMVIXHTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-5-硝基苯酚 在 盐酸 、 tin(II)chloride dihydrate 、 caesium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 15.0h， 生成 N-(3-((2-bromobenzyl)oxy)-4-chlorophenyl)-4-methoxypyrimidin-2-amine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3-benzyloxy-linked pyrimidinylphenylamine derivatives as potent HIV-1 NNRTIs

  摘要：

  A novel series of 3-benzyloxy-linked pyrimidinylphenylamine derivatives (8a-8s) was designed, synthesized and evaluated for their in vitro anti-HIV activity in MT-4 cell cultures. Most of the compounds inhibited wild-type (wt) HIV-1 replication in the lower micromolar concentration range (EC50 = 0.05-35 mu M) with high selectivity index (SI) values (ranged from 10 to >4870). In particular, 8h and 8g displayed excellent antiretroviral activity against wt HIV-1 with low cytotoxicity (EC50 = 0.07 mu M, CC50 >347 mu M, SI >4870; EC50 = 0.05 mu M, CC50 = 42 mu M, SI = 777, respectively), comparable to that of the marked drug nevirapine (EC50 = 0.113 mu M, CC50 >15 mu M, SI >133). In order to confirm the binding target, 8h was selected to perform the anti-HIV-1 RT assay. Additionally, preliminary structure activity relationship (SAR) analysis and molecular docking studies of newly synthesized compounds were also discussed, as well as the predicted physicochemical properties. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.051

文献信息

• Design, synthesis and biological evaluation of 3-benzyloxy-linked pyrimidinylphenylamine derivatives as potent HIV-1 NNRTIs
  作者：Diwakar Rai、Wenmin Chen、Ye Tian、Xuwang Chen、Peng Zhan、Erik De Clercq、Christophe Pannecouque、Jan Balzarini、Xinyong Liu

  DOI：10.1016/j.bmc.2013.09.051

  日期：2013.12

  A novel series of 3-benzyloxy-linked pyrimidinylphenylamine derivatives (8a-8s) was designed, synthesized and evaluated for their in vitro anti-HIV activity in MT-4 cell cultures. Most of the compounds inhibited wild-type (wt) HIV-1 replication in the lower micromolar concentration range (EC50 = 0.05-35 mu M) with high selectivity index (SI) values (ranged from 10 to >4870). In particular, 8h and 8g displayed excellent antiretroviral activity against wt HIV-1 with low cytotoxicity (EC50 = 0.07 mu M, CC50 >347 mu M, SI >4870; EC50 = 0.05 mu M, CC50 = 42 mu M, SI = 777, respectively), comparable to that of the marked drug nevirapine (EC50 = 0.113 mu M, CC50 >15 mu M, SI >133). In order to confirm the binding target, 8h was selected to perform the anti-HIV-1 RT assay. Additionally, preliminary structure activity relationship (SAR) analysis and molecular docking studies of newly synthesized compounds were also discussed, as well as the predicted physicochemical properties. (C) 2013 Elsevier Ltd. All rights reserved.