4-[[4-(Methylamino)-6-(2-naphthyloxy)-1,3,5-triazin-2-yl]amino]benzonitrile | 1042420-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[[4-(Methylamino)-6-(2-naphthyloxy)-1,3,5-triazin-2-yl]amino]benzonitrile
• 英文别名: 4-[[4-(methylamino)-6-naphthalen-2-yloxy-1,3,5-triazin-2-yl]amino]benzonitrile
• CAS: 1042420-61-0
• 化学式: C₂₁H₁₆N₆O
• 分子量: 368.398
• InChiKey: AHDAQYBLWRRAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-[4-chloro-6-(2-naphthyloxy)-1,3,5-triazin-2-yl]aminobenzonitrile 、 甲胺 以 1,4-二氧六环 为溶剂， 以37.9%的产率得到4-[[4-(Methylamino)-6-(2-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

文献信息

• Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 11: Structural modulations of diaryltriazines with potent anti-HIV activity
  作者：Yuan-Zhen Xiong、Fen-Er Chen、Jan Balzarini、Erik De Clercq、Christophe Pannecouque

  DOI：10.1016/j.ejmech.2007.08.001

  日期：2008.6

  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.