4-[4-chloro-6-(1-naphthyloxy)-1,3,5-triazin-2-yl]aminobenzonitrile | 139910-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[4-chloro-6-(1-naphthyloxy)-1,3,5-triazin-2-yl]aminobenzonitrile
• 英文别名: 4-[(4-chloro-6-naphthalen-1-yloxy-1,3,5-triazin-2-yl)amino]benzonitrile
• CAS: 139910-38-6
• 化学式: C₂₀H₁₂ClN₅O
• 分子量: 373.801
• InChiKey: YZMRDGVTZAIRIT-UHFFFAOYSA-N

物化性质

• 熔点：
  224.0-224.5 °C(Solv: methanol (67-56-1))
• 沸点：
  637.3±57.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[4-chloro-6-(1-naphthyloxy)-1,3,5-triazin-2-yl]aminobenzonitrile 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 以33.5%的产率得到4-[[4-Amino-6-(1-naphthyloxy)-1,3,5-triazin-2-yl]amino]benzonitrile
  参考文献：
  名称：

  Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 11: Structural modulations of diaryltriazines with potent anti-HIV activity

  摘要：

  A series of novel 6-naphthyloxy substituted DATA analogues bearing different substituents on the C-6 position of triazine ring were synthesized and evaluated for their in vitro anti-HIV activity in MT-4 cells. The results demonstrated that most of the compounds in this series are potent activity against HIV-1 with moderate to high selectivity. Among these analogues, two compounds exhibited excellent effect in inhibiting HIV-1 replication at nanomolar concentration (for compound 9h: IC(50) = 9.3 nM, SI = 15,385; for compound 9i: IC(50) = 9.4 nM, SI = 14,094), which are about 15-fold more active than nevirapine. In addition, several compounds are active against both HIV-1 and HIV-2, whose mechanism may be different from typical NNRTIs. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.001
• 作为产物：
  描述：

  萘酚 、 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzonitrile 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以50.67%的产率得到4-[4-chloro-6-(1-naphthyloxy)-1,3,5-triazin-2-yl]aminobenzonitrile
  参考文献：
  名称：

  Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 11: Structural modulations of diaryltriazines with potent anti-HIV activity

  摘要：

  A series of novel 6-naphthyloxy substituted DATA analogues bearing different substituents on the C-6 position of triazine ring were synthesized and evaluated for their in vitro anti-HIV activity in MT-4 cells. The results demonstrated that most of the compounds in this series are potent activity against HIV-1 with moderate to high selectivity. Among these analogues, two compounds exhibited excellent effect in inhibiting HIV-1 replication at nanomolar concentration (for compound 9h: IC(50) = 9.3 nM, SI = 15,385; for compound 9i: IC(50) = 9.4 nM, SI = 14,094), which are about 15-fold more active than nevirapine. In addition, several compounds are active against both HIV-1 and HIV-2, whose mechanism may be different from typical NNRTIs. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.001