N6-(4-methoxy-benzylidene)-quinazoline-2,4,6-triamine | 13953-69-0

• 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: N6-(4-methoxy-benzylidene)-quinazoline-2,4,6-triamine
• 英文别名: N⁶-(4-methoxy-benzylidene)-quinazoline-2,4,6-triamine
• CAS: 13953-69-0
• 化学式: C₁₆H₁₅N₅O
• 分子量: 293.328
• InChiKey: GKAPDMQTVADMRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  99.41
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N6-(4-methoxy-benzylidene)-quinazoline-2,4,6-triamine 在 sodium tetrahydroborate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 180.0h， 生成 N⁶,N⁶-di(4-methoxybenzyl)quinazoline-2,4,6-triamine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of quinazoline derivatives as anti-trypanosomatid and anti-plasmodial agents

  摘要：

  In this paper, the design, synthesis and biological evaluation of a set of quinazoline-2,4,6-triamine derivatives (1-9) as trypanocidal, antileishmanial and antiplasmodial agents are explained. The compounds were rationalized basing on docking studies of the dihydrofolate reductase (DHFR from Trypanosoma cruzi, Leishmania major and Plasmodium vivax) and pteridin reductase (PTR from T. cruzi and L major) structures. All compounds were in vitro screened against both bloodstream trypomastigotes of T cruzi (NINOA and INC-5 strains) and prornatigotes of Leishmania mexicana (MHOM/BZ/61/M379 strain), and also for cytotoxicity using Vero cell line. Against T. cruzi, three compounds (5, 6 and 8) were the most effective showing a better activity profile than nifurtimox and benznidazole (reference drugs). Against L. mexicana, four compounds (5, 6, 8, and 9) exhibited the highest activity, even than glucantime (reference drug). In the cytotoxicity assay, protozoa were more susceptible than Vero cells. In vivo Plasmodium berghei assay (ANKA strain), the compounds 1, 5, 6 and 8 showed a more comparable activity than chloroquine and pyrimethamine (reference drugs) when they were administrated by the oral route. The antiprotozoal activity of these substances, endowed with redox properties, represented a good starting point for a medicinal chemistry program aiming for chemotherapy of Chagas' disease, leishmaniosis and malaria. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.028
• 作为产物：
  描述：

  2,4-二氨基-6-硝基喹唑啉 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0~110.0 ℃ 、413.7 kPa 条件下， 反应 61.0h， 生成 N6-(4-methoxy-benzylidene)-quinazoline-2,4,6-triamine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of quinazoline derivatives as anti-trypanosomatid and anti-plasmodial agents

  摘要：

  In this paper, the design, synthesis and biological evaluation of a set of quinazoline-2,4,6-triamine derivatives (1-9) as trypanocidal, antileishmanial and antiplasmodial agents are explained. The compounds were rationalized basing on docking studies of the dihydrofolate reductase (DHFR from Trypanosoma cruzi, Leishmania major and Plasmodium vivax) and pteridin reductase (PTR from T. cruzi and L major) structures. All compounds were in vitro screened against both bloodstream trypomastigotes of T cruzi (NINOA and INC-5 strains) and prornatigotes of Leishmania mexicana (MHOM/BZ/61/M379 strain), and also for cytotoxicity using Vero cell line. Against T. cruzi, three compounds (5, 6 and 8) were the most effective showing a better activity profile than nifurtimox and benznidazole (reference drugs). Against L. mexicana, four compounds (5, 6, 8, and 9) exhibited the highest activity, even than glucantime (reference drug). In the cytotoxicity assay, protozoa were more susceptible than Vero cells. In vivo Plasmodium berghei assay (ANKA strain), the compounds 1, 5, 6 and 8 showed a more comparable activity than chloroquine and pyrimethamine (reference drugs) when they were administrated by the oral route. The antiprotozoal activity of these substances, endowed with redox properties, represented a good starting point for a medicinal chemistry program aiming for chemotherapy of Chagas' disease, leishmaniosis and malaria. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.028