6-(2-吡啶基)-1,3,5-三嗪-2,4-二胺 | 25007-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 6-(2-吡啶基)-1,3,5-三嗪-2,4-二胺
• 英文名称: 2,4-diamino-6-(2-pyridyl)-1,3,5-triazine
• 英文别名: 6-(pyridin-2-yl)-1,3,5-triazine-2,4-diamine；2,4-diamino-6-pyridyl-1,3,5-triazine；2,6-Diamino-4-(2-pyridyl)-s-triazine；6-pyridin-2-yl-1,3,5-triazine-2,4-diamine
• CAS: 25007-79-8
• 化学式: C₈H₈N₆
• 分子量: 188.192
• InChiKey: MTSVIHVYYVZVLK-UHFFFAOYSA-N

物化性质

• 熔点：
  297-298 °C(Solv: water (7732-18-5))
• 沸点：
  544.1±42.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-(2-吡啶基)-1,3,5-三嗪-2,4-二胺 在 溶剂黄146 、 亚硝酸异戊酯 作用下， 以 水 为溶剂， 以55%的产率得到4-amino-6-(pyridin-2-yl)-1,3,5-triazin-2-ol
  参考文献：
  名称：

  Synthesis of O2- and N3-(2-Phosphonomethoxy)ethyl Derivatives of 6-Phenyl- and 6-Pyridinyl-5-azacytosine

  摘要：

  A series of hydrolytically stable O-2- and N-3-(2-phosphonomethoxy)ethyl (PME) derivatives of 6-phenyl, pyridin-2, -3 and -4-yl-5-azacytosines was prepared by their alkylation with diisopropyl (2-chloroethoxy)methylphosphonate followed by the deprotection. No antitumor or antiviral activity was found except for 6-(pyridin-4-yl)-1,3,5-triazine-2,4-diamine (13d) which exhibited slight activity against feline herpesvirus in CrFK cell cultures with IC50 = 6.7 mu g/mL.

  DOI：

  10.3987/com-11-12137
• 作为产物：
  描述：

  2-氰基吡啶 、 二聚氰胺 在 potassium hydroxide 作用下， 以 乙二醇甲醚 为溶剂， 反应 4.0h， 以92.1%的产率得到6-(2-吡啶基)-1,3,5-三嗪-2,4-二胺
  参考文献：
  名称：

  Synthesis and Crystal Structure of Two Polydimensional Molecular Architectures from Cobalt(II), Copper(II) Complexes of 2,4-Diamino-6-pyridyl-1,3,5-triazine

  摘要：

  合成并结构表征了两种新型的2,4-二氨基-6-吡啶基-1,3,5-三嗪（ptzda）的钴(II)和铜(II)配合物。晶体结构研究表明，钴原子受四个来自四个二氰胺阴离子的氮原子和另外两个来自2,4-二氨基-6-吡啶基-1,3,5-三嗪的氮原子的六配位，每个钴原子通过两个[N(CN)2]–阴离子连接，形成无限双链桥接结构，形成二维梯子状的构型。而铜原子则由两个来自两个二氰胺阴离子的氮原子和另外两个来自2,4-二氨基-6-吡啶基-1,3,5-三嗪的氮原子五配位，每个铜原子通过一个甲醇连接，形成无限双链桥接结构，形成一维梯子状的构型。

  DOI：

  10.14233/ajchem.2014.15424

文献信息

• Water-soluble DNA minor groove binders as potential chemotherapeutic agents: synthesis, characterization, DNA binding and cleavage, antioxidation, cytotoxicity and HSA interactions
  作者：Xia-Bing Fu、Dan-Dan Liu、Yuan Lin、Wei Hu、Zong-Wan Mao、Xue-Yi Le

  DOI：10.1039/c3dt53577k

  日期：——

  Two new water-soluble copper(II)-dipeptide complexes: [Cu(glygly)(PyTA)]ClO4·1.5H2O (1) and [Cu(glygly)(PzTA)]ClO4·1.5H2O (2) (glygly = glycylglycine anion, PyTA = 2,4-diamino-6-(2′-pyridyl)-1,3,5-triazine and PzTA = 2,4-diamino-6-(2′-pyrazino)-1,3,5-triazine), utilizing two interrelated DNA base-like ligands (PyTA and PzTA), have been synthesized and characterized. The structure elucidation for 1 performed by single crystal X-ray diffraction showed a one dimensional chain conformation in which the central copper ions arrange in a five-coordinate distorted square-pyramidal geometry. Spectroscopic titration, viscosity and electrophoresis measurements revealed that the complexes bound to DNA via an outside groove binding mode, and cleaved pBR322 DNA efficiently in the presence of ascorbate, probably via an oxidative mechanism with the involvement of ˙OH and ˙O2−. Notably, the complexes exhibited considerable in vitro cytotoxicity against four human carcinoma cell lines (HepG2, HeLa, A549 and U87) with IC50 values ranging from 41.68 to 159.17 μM, in addition to their excellent SOD mimics (IC50 ∼ 0.091 and 0.114 μM). Besides, multispectroscopic evidence suggested their HSA-binding at the cavity containing Trp-214 in subdomain IIA with moderate affinity, mainly via hydrophobic interaction. Further, the molecular docking technique utilized for ascertaining the mechanism and mode of action towards DNA and HSA theoretically verified the experimental results.

  两种新的水溶性铜(II)二肽配合物：[Cu(甘甘)(PyTA)]ClO4·1.5H2O (1) 和 [Cu(甘甘)(PzTA)]ClO4·1.5H2O (2) (甘甘 = 甘氨酰甘氨酸阴离子，PyTA = 2,4-二氨基-6-(2'-吡啶基)-1,3,5-三嗪，PzTA = 2,4-二氨基-6-(2'-吡嗪基)-1,3,5-三嗪)，利用两种相关的类DNA碱基配体(PyTA和PzTA)，已合成并表征。通过单晶X射线衍射对1的结构解析显示为一维链状构型，其中央铜离子排列在五配位扭曲的四角锥几何结构中。光谱滴定、粘度和电泳测量揭示了配合物通过外部沟槽结合模式与DNA结合，并在抗坏血酸盐存在下高效切割pBR322 DNA，可能通过涉及˙OH和˙O2-的氧化机制。值得注意的是，配合物对四种人癌细胞系(HepG2、HeLa、A549和U87)显示出相当大的体外细胞毒性，IC50值范围从41.68到159.17 μM，此外它们还具有优秀的SOD模拟(IC50 ∼ 0.091和0.114 μM)。此外，多光谱证据表明它们在含有Trp-214的亚域IIA腔中与HSA结合，主要通过疏水相互作用，具有适度亲和力。进一步，利用分子对接技术理论上验证了实验结果，确定了其对DNA和HSA的作用机制和模式。
• Direct Conversion of Aldehydes to Amides, Tetrazoles, and Triazines in Aqueous Media by One-Pot Tandem Reactions
  作者：Jiun-Jie Shie、Jim-Min Fang

  DOI：10.1021/jo026407z

  日期：2003.2.1

  A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in modest to high yields. The one-pot tandem reactions were conducted in water media, and the products were obtained simply by extraction

  在室温下，各种醛在氨水中与碘反应生成腈中间体，通过添加过氧化氢，叠氮化钠或双氰胺将其捕集，以生成相应的酰胺，四唑和1,3,5-三嗪中等至高产。一锅串联反应在水介质中进行，只需萃取或过滤即可获得产物。
• Cis–trans isomerism modulates the magnetic relaxation of dysprosium single-molecule magnets
  作者：Jianfeng Wu、Julie Jung、Peng Zhang、Haixia Zhang、Jinkui Tang、Boris Le Guennic

  DOI：10.1039/c5sc04510j

  日期：——

  Geometry and magnetic relaxation modulations in a series of mononuclear dysprosium complexes, [DyLz2(o-vanilin)2]·X·solvent (Lz = 6-pyridin-2-yl-[1,3,5]triazine-2,4-diamine; X = Br− (1), NO3− (2), CF3SO3− (3)), were realized by changing the nature of the counter-anion. The DyIII ions in all complexes are eight-coordinate and in approximate D4d symmetry environments. The magnetic relaxation and anisotropy

  一系列单核络合物[DyLz 2（o -vanilin）2 ]·X·溶剂（Lz = 6-吡啶-2-基-[1,3,5]三嗪-2,4 ）的几何和磁弛豫调制二胺; X = Br的- （1），NO 3 - （2），CF 3 SO 3 - （3））中，通过改变反阴离子的性质来实现。所有络合物中的Dy III离子均为八坐标，且处于近似D 4d对称环境中。从实验上和实验上系统地研究了这些配合物的磁弛豫和各向异性从头算起。所有复合物均表现出优异的单分子磁行为。值得注意的是，磁结构研究表明，配合物2中方形反棱角环境的协调平面的旋转会诱导通过较高激发态的磁弛豫路径，从而产生615 K（对于稀释样品为696 K）的高各向异性势垒。此外，在最高7 K的温度下观察到明显的磁滞回线打开，这是ever单分子磁体有史以来的最高阻断温度。
• Versatile Rh- and Ir-Based Catalysts for CO₂ Hydrogenation, Formic Acid Dehydrogenation, and Transfer Hydrogenation of Quinolines
  作者：Jairo Fidalgo、Margarita Ruiz-Castañeda、Gabriel García-Herbosa、Arancha Carbayo、Félix A. Jalón、Ana M. Rodríguez、Blanca R. Manzano、Gustavo Espino

  DOI：10.1021/acs.inorgchem.8b02164

  日期：2018.11.19

  coordinated or not to the metal center, were used. The general formula of the new complexes are [(p-cymene)RuCl(N,N′)]X, X = Cl–, BF4– and [Cp*MCl(N,N′)]Cl, M = Rh, Ir, where the N,N′ ligands are 8-aminoquinoline (HL1), 6-pyridyl-2,4-diamine-1,3,5-triazine (L2) and 5-amino-1,10-phenanthroline (L3). Some complexes are not active or catalyze only one process. However, the complexes [Cp*MCl(HL1)]Cl with M

  考虑到对与氢存储相关的过程（例如CO 2氢化和甲酸（FA）分解）的兴趣，我们合成了一组Ir，Rh或Ru络合物作为这些反应中的通用预催化剂进行测试。关于由FA形成H 2，已经解决了这些络合物在具有挑战性的底物的转移氢化（TH）中使用FA /甲酸酯作为氢供体的喹啉衍生物的可能适用性。考虑到二级配位球相互作用的重要性，使用了含或不与金属中心配位的NH 2基团的N，N'配体。新络合物的通式为[（p -cymene）RuCl（N，N'）] X，X = Cl –，BF 4 –和[Cp * MCl（N，N'）] Cl，M = Rh，Ir，其中N，N'配体为8-氨基喹啉（HL1），6-吡啶基-2,4-二胺-1 ，3,5-三嗪（L2）和5-氨基-1,10-菲咯啉（L3）。某些配合物不具有活性或仅催化一个过程。然而，配合物[Cp * MCl（HL1）] Cl与M = Rh，Ir是多功能催化剂，它们在喹啉加氢，FA分解以及CO
• Synthesis, crystal structures, molecular docking and in vitro cytotoxicity studies of two new copper(<scp>ii</scp>) complexes: special emphasis on their binding to HSA
  作者：Fang Shen、Ya-Xian Liu、Shu-Min Li、Chi-Kun Jiang、Bing-Feng Wang、Ya-Hong Xiong、Zong-Wan Mao、Xue-Yi Le

  DOI：10.1039/c7nj02351k

  日期：——

  that the binding sites of the complexes on HSA were close to Trp-214 residue in IIA subdomain, which was further verified by site marker competitive experiments and molecular docking method. Moreover, the in vitro cytotoxicity experiments showed that the effective HSA-binding interactions enhanced the cytotoxicity of the complexes. Inspiringly, both 1 and 2 displayed strong anticancer activities against

  两种新的混合配体铜（II）配合物[Cu（PyTA）（L -Phe）Cl]·2H 2 O（1），[Cu（PyTA）（L -Met）Cl]·0.5H 2 O（2 ）（其中PyTA = 2,4-二氨基-6-（2'-吡啶基）-1,3,5-三嗪，L -Phe = L-苯丙氨酸，L -Met = L-蛋氨酸）并进行了表征元素分析，IR，UV-vis，摩尔电导率，ESI-MS和X射线晶体衍射。1和2的铜中心是在略微扭曲的方形金字塔环境中发现的。荧光猝灭实验和量热技术表明，该复合物以高亲和力与人血清白蛋白（HSA）结合（结合常数KD = 3.71×10 6 L·mol -1为1和1.99×10 6 L·mol -1为2，1 > 2）。紫外可见光谱和圆二色性（CD）光谱表明，该络合物在结合过程中诱导了疏水环境的改变，并降低了HSA的α-螺旋水平。此外，同步荧光光谱表明，HSA上复合物的结合位点接近IIA亚域