N,N'-(6-aminoquinazoline-2,4-diyl)diacetamide | 27339-13-5

• 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: N,N'-(6-aminoquinazoline-2,4-diyl)diacetamide
• 英文别名: N-(2-acetamido-6-aminoquinazolin-4-yl)acetamide
• CAS: 27339-13-5
• 化学式: C₁₂H₁₃N₅O₂
• 分子量: 259.268
• InChiKey: HDYNACHYRKJETI-UHFFFAOYSA-N

物化性质

• 密度：
  1.452±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-(6-aminoquinazoline-2,4-diyl)diacetamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 N⁶-(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-氰基-4-硝基苯胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 20.0~100.0 ℃ 、413.7 kPa 条件下， 反应 19.33h， 生成 N,N'-(6-aminoquinazoline-2,4-diyl)diacetamide
  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

• N6-(FERROCENMETHYL)QUINAZOLIN-2,4,6-TRIAMINA (H2) AND THE DERIVATIVES AND PRODRUGS THEREOF AS ANTILEISHMANIAL, ANTIPROTOZOAL, ANTIPARASITIC AND ANTIMICROBIAL AGENTS
  申请人：Galindo Sevilla Norma del Carmen

  公开号：US20130109663A1

  公开（公告）日：2013-05-02

  The use of N 6 -(ferrocenmethyl)quinazoline-2,4,6-triamine (H2), its derivatives, and prodrugs that present antimicrobial (antibiotic, microbicide), antiparasitic (parasiticide), antiprotozoal (protozoacide), and antileishmanial (leishmanicide) activities, as well as its use as a drug in vertebrates (humans and animals).

  使用N6-(ferrocenmethyl)quinazoline-2,4,6-triamine（H2）及其衍生物和前药，具有抗微生物（抗生素，微生物杀灭剂），抗寄生虫（寄生虫杀灭剂），抗原虫（原虫杀灭剂）和抗利什曼病（利什曼菌杀灭剂）活性，并将其用作脊椎动物（人类和动物）的药物。
• N6-(FERROCENMETHYL)QUINAZOLIN-2,4,6-TRIAMIN (H2) AND THE DERIVATIVES AND PRODRUGS THEREOF AS ANTILEISHMANIAL, ANTIPROTOZOAL, ANTIPARASITIC AND ANTIMICROBIAL AGENTS
  申请人：Galindo Sevilla, Norma Del Carmen

  公开号：EP2599783B1

  公开（公告）日：2016-12-14
• US8664384B2
  申请人：——

  公开号：US8664384B2

  公开（公告）日：2014-03-04