N²-methyl-2,4-diamino-6-hydrazinyl-[1,3,5]triazine | 94793-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N²-methyl-2,4-diamino-6-hydrazinyl-[1,3,5]triazine
• 英文别名: 6-Hydrazinyl-N~2~-methyl-1,3,5-triazine-2,4-diamine；6-hydrazinyl-2-N-methyl-1,3,5-triazine-2,4-diamine
• CAS: 94793-96-1
• 化学式: C₄H₉N₇
• mdl: MFCD19201815
• 分子量: 155.162
• InChiKey: MTSUDGZBVPNPPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-methyl-2,4-diamino-6-hydrazinyl-[1,3,5]triazine 、 5-硝基糠醛 以 甲醇 为溶剂， 生成 4-N-methyl-2-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Design and Synthesis of a Series of Melamine-based Nitroheterocycles with Activity against Trypanosomatid Parasites

  摘要：

  The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T cruzi against which various nitro heterocycles are already registered for use.

  DOI：

  10.1021/jm050177+
• 作为产物：
  描述：

  2-氯-4-甲基氨基-6-氨基-1,3,5-三嗪- 在 一水合肼 作用下， 以 水 为溶剂， 以30%的产率得到N²-methyl-2,4-diamino-6-hydrazinyl-[1,3,5]triazine
  参考文献：
  名称：

  Design and Synthesis of a Series of Melamine-based Nitroheterocycles with Activity against Trypanosomatid Parasites

  摘要：

  The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T cruzi against which various nitro heterocycles are already registered for use.

  DOI：

  10.1021/jm050177+

文献信息

• Fullerene derivatized s-triazine analogues as antimicrobial agents
  作者：Anish Kumar、Shobhana Karuveettil Menon

  DOI：10.1016/j.ejmech.2008.10.036

  日期：2009.5

  A series of novel fullerene derivatives bearing s-triazine moiety have been synthesized by adopting 1,3 dipolar cycloaddition reaction of C60 and azomethine ylides generated from the corresponding Schiff bases of 2,4,6 trisubstituted s-triazine. All the compounds synthesized were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR and FAB-MS. The compounds were then screened for their antibacterial

  通过采用C 60的1，3偶极环加成反应和由2，4，6三取代的s－三嗪的相应席夫碱生成的偶氮甲碱，合成了一系列带有s－三嗪部分的富勒烯衍生物。通过元素分析，FT-IR，1 H NMR，13 C NMR和FAB-MS对合成的所有化合物进行表征。然后筛选化合物对革兰氏阳性（金黄色葡萄球菌，枯草芽孢杆菌，枯草芽孢杆菌）和革兰氏阴性（大肠杆菌，铜绿假单胞菌和通过圆盘扩散法分离出肺炎克雷伯菌。发现所有化合物均以非常低的浓度对这些菌株具有活性，并且与标准药物环丙沙星相当。
• Design and Synthesis of a Series of Melamine-based Nitroheterocycles with Activity against Trypanosomatid Parasites
  作者：Alessandro Baliani、Gorka Jimenez Bueno、Mhairi L. Stewart、Vanessa Yardley、Reto Brun、Michael P. Barrett、Ian H. Gilbert

  DOI：10.1021/jm050177+

  日期：2005.8.1

  The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T cruzi against which various nitro heterocycles are already registered for use.