4-{[(2,4-diaminoquinazolin-6-yl)amino]methyl}phenol | 13794-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-{[(2,4-diaminoquinazolin-6-yl)amino]methyl}phenol
• 英文别名: 4-[(2,4-diamino-quinazolin-6-ylamino)-methyl]-phenol；4-[[(2,4-Diaminoquinazolin-6-yl)amino]methyl]phenol
• CAS: 13794-59-7
• 化学式: C₁₅H₁₅N₅O
• 分子量: 281.317
• InChiKey: LTQKXZTUYJOLPK-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  649.0±65.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 100.0 ℃ 、413.7 kPa 条件下， 反应 127.33h， 生成 4-{[(2,4-diaminoquinazolin-6-yl)amino]methyl}phenol
  参考文献：
  名称：

  Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies

  摘要：

  A series of quinazoline-2,4,6-triamine were synthesized and evaluated in vitro against Leishmania mexicana. Among them, N-6-(ferrocenmethyl)quinazolin-2,4,6-triamine (II2) showed activity on promastigotes and intracellular amastigotes, as well as low cytotoxicity in mammalian cells. Docking and electrochemical studies showed the importance of both the ferrocene and the heterocyclic nucleus to the observed activity. 142 is readily oxidized electrochemically, indicating that the mechanism of action probably involves redox reactions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.051

文献信息

• Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies
  作者：Cesar Mendoza-Martínez、Norma Galindo-Sevilla、José Correa-Basurto、Victor Manuel Ugalde-Saldivar、Rosa Georgina Rodríguez-Delgado、Jessica Hernández-Pineda、Cecilia Padierna-Mota、Marcos Flores-Alamo、Francisco Hernández-Luis

  DOI：10.1016/j.ejmech.2014.12.051

  日期：2015.3

  A series of quinazoline-2,4,6-triamine were synthesized and evaluated in vitro against Leishmania mexicana. Among them, N-6-(ferrocenmethyl)quinazolin-2,4,6-triamine (II2) showed activity on promastigotes and intracellular amastigotes, as well as low cytotoxicity in mammalian cells. Docking and electrochemical studies showed the importance of both the ferrocene and the heterocyclic nucleus to the observed activity. 142 is readily oxidized electrochemically, indicating that the mechanism of action probably involves redox reactions. (C) 2014 Elsevier Masson SAS. All rights reserved.