6-(bromomethyl)-N²,N²-dimethyl-1,3,5-triazine-2,4-diamine | 36283-04-2

• 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: 6-(bromomethyl)-N²,N²-dimethyl-1,3,5-triazine-2,4-diamine
• 英文别名: 6-(bromomethyl)-2-N,2-N-dimethyl-1,3,5-triazine-2,4-diamine
• CAS: 36283-04-2
• 化学式: C₆H₁₀BrN₅
• 分子量: 232.083
• InChiKey: MDTKZHYLBWKSFE-UHFFFAOYSA-N

物化性质

• 沸点：
  398.1±44.0 °C(Predicted)
• 密度：
  1.671±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(bromomethyl)-N²,N²-dimethyl-1,3,5-triazine-2,4-diamine 、 di-tert-butyl dodecane-1,12-diylbis((3-aminopropyl)carbamate) 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of s-Triazine Substituted Polyamines as Potential New Anti-Trypanosomal Drugs

  摘要：

  The P2 transporter is a nucleoside transporter which is unique to the protozoan parasite Trypanosoma brucei, the causative organism of Human African Trypanosomasis. The transporter has been shown to bind some structural motifs not recognized by other transporters. In this paper we describe the use of the melamine motif, a substrate of the P2 transporter, as a potential tool to selectively deliver polyamine analogues to the parasites. The synthesis of a number of polyamine analogues attached to a variety of melamine analogues is described. Many of the compounds were shown to competitively inhibit uptake of adenosine, indicating that they are recognized by the transporter. Some of the compounds showed good in vitro activity against the parasites.

  DOI：

  10.1021/jm010854+
• 作为产物：
  描述：

  溴乙酸甲酯 、 盐酸二甲双胍 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以79.28 %的产率得到6-(bromomethyl)-N²,N²-dimethyl-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  取代 18β-甘草次酸 3-乙酰基-30-N2, N2-二甲基-1', 3', 5'-三嗪-2', 4'-二胺的合成、光谱表征、晶体结构、DFT 计算和 Hirshfeld 表面分析化合物

  摘要：

  18β-甘草次酸（GA）化合物广泛存在于药物分子中，具有良好的生物活性。许多文献报道了18β-GA衍生物的抗肿瘤活性，其中一些化合物表现出比18β-GA本身和吉非替尼更好的抗肿瘤活性。化合物1是18β-甘草次酸化合物之一(4-氨基-6-(二甲氨基)-1,3,5-三嗪-2-基)甲基(2S,6aS,8aR,12bR)-10-乙酰氧基- 2,4a,6a,6b,9,9,12a-七甲基-13-氧代-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,设计合成了12,12a,12b,13,14b-二十碳氢芫烯-2-羧酸酯，并通过UV-vis、FT-IR、Raman、NMR( 1 H, 13 C) 和 HRMS。使用单晶X射线衍射分析了1的精确结构，并显示出有趣的分子间N H … O和N H ... H/H … N 联系人。

  DOI：

  10.1016/j.molstruc.2023.137296

文献信息

• Synthesis, spectroscopic characterization, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-acetyl-30-N, N-dimethyl-1′, 3′, 5′-triazine-2′, 4′-diamine of substituted 18β-Glycyrrhetinic compound
  作者：Yixia Gong、Yuqing Chen、Deqi Kong、Mingyu Huang、Xueli Bai、Yiding Geng

  DOI：10.1016/j.molstruc.2023.137296

  日期：2024.3

  the molecular structure optimized by DFT were consistent with the crystal structures determined by single crystal X-ray diffraction. The molecular electrostatic potential and frontier molecular orbitals of the title compound were further investigated by DFT, and some physicochemical properties of the compound are revealed. In additional, the intermolecular interactions in the crystal were investigated

  18β-甘草次酸（GA）化合物广泛存在于药物分子中，具有良好的生物活性。许多文献报道了18β-GA衍生物的抗肿瘤活性，其中一些化合物表现出比18β-GA本身和吉非替尼更好的抗肿瘤活性。化合物1是18β-甘草次酸化合物之一(4-氨基-6-(二甲氨基)-1,3,5-三嗪-2-基)甲基(2S,6aS,8aR,12bR)-10-乙酰氧基- 2,4a,6a,6b,9,9,12a-七甲基-13-氧代-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,设计合成了12,12a,12b,13,14b-二十碳氢芫烯-2-羧酸酯，并通过UV-vis、FT-IR、Raman、NMR( 1 H, 13 C) 和 HRMS。使用单晶X射线衍射分析了1的精确结构，并显示出有趣的分子间N H … O和N H ... H/H … N 联系人。
• Synthesis and Biological Evaluation of <i>s</i>-Triazine Substituted Polyamines as Potential New Anti-Trypanosomal Drugs
  作者：Burkhard Klenke、Mhairi Stewart、Michael P. Barrett、Reto Brun、Ian H. Gilbert

  DOI：10.1021/jm010854+

  日期：2001.10.1

  The P2 transporter is a nucleoside transporter which is unique to the protozoan parasite Trypanosoma brucei, the causative organism of Human African Trypanosomasis. The transporter has been shown to bind some structural motifs not recognized by other transporters. In this paper we describe the use of the melamine motif, a substrate of the P2 transporter, as a potential tool to selectively deliver polyamine analogues to the parasites. The synthesis of a number of polyamine analogues attached to a variety of melamine analogues is described. Many of the compounds were shown to competitively inhibit uptake of adenosine, indicating that they are recognized by the transporter. Some of the compounds showed good in vitro activity against the parasites.
• Synthesis, spectroscopic characterization, crystal structure, DFT calculations, Hirshfeld surface analysis and anti-cancer activities of (4-amino-6-(dimethylamino)-1,3,5-triazin-2-yl)methyl 2-acetoxybenzoate compound
  作者：Yiding Geng、Xueli Bai、Mingyu Huang、Deqi Kong、Yuqing Chen、Yixia Gong

  DOI：10.1016/j.molstruc.2024.138053

  日期：2024.7

  esterification from metformin hydrochloride as the starting material. (4-amino-6-(dimethylamino)-1,3,5-triazin-2-yl)methyl 2-acetoxybenzoate was designed and synthesized, and the structure was characterized by spectroscopic techniques including UV–vis, FT-IR, FT-Raman, H NMR, C NMR and HRMS. The single crystal structure of the target molecule was confirmed by X-ray diffraction and showed intermolecular

  1,3,5-三嗪类化合物具有抗肿瘤等生物活性。本论文以盐酸二甲双胍为原料，经环化、酯化合成了标题化合物。设计并合成了(4-氨基-6-(二甲氨基)-1,3,5-三嗪-2-基)甲基2-乙酰氧基苯甲酸酯，并通过UV-vis、FT-IR、FT等光谱技术对其结构进行了表征-拉曼、1H NMR、13C NMR 和 HRMS。通过X射线衍射证实了目标分子的单晶结构，并显示出分子间NHO、NHN、CHO氢键，这是晶体堆积相互作用中最重要的因素。还提供了分子的几何参数、分子静电势 (MEP) 和前沿分子轨道 (FMO) 分析，以揭示所研究化合物的物理化学性质。此外，通过使用晶体信息文件对标题分子进行 Hirshfeld 表面分析，对晶体堆积的显着贡献来自 OH/H2O 接触。我们分析了标题化合物的体外抗肿瘤活性，在A549中的IC50值为10.55 μM。分子对接结果表明，标题化合物对DEPTOR（7DKL