6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine | 2515-30-2

• 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-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine
• 英文别名: 6-chloro-N²,N⁴-di(p-tolyl)-1,3,5-triazine-2,4-diamine；6-chloro-N²,N⁴-di-p-tolyl-1,3,5-triazine-2,4-diamine；6-chloro-N(2),N(4)-dip-tolyl-1,3,5-triazine-2,4-diamine；6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine；1,3,5-Triazine-2,4-diamine, 6-chloro-N,N'-bis(4-methylphenyl)-；6-chloro-2-N,4-N-bis(4-methylphenyl)-1,3,5-triazine-2,4-diamine
• CAS: 2515-30-2
• 化学式: C₁₇H₁₆ClN₅
• mdl: MFCD00392454
• 分子量: 325.801
• InChiKey: QNBNEVDEANWKFB-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C(Solv: benzene (71-43-2))
• 沸点：
  528.6±53.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.5h， 生成 4-[[4,6-bis(4-methylanilino)-1,3,5-triazin-2-yl]amino]-N'-(4-methylphenyl)sulfonylbenzohydrazide
  参考文献：
  名称：

  Langalia, N. A.; Thaker, K. A., Journal of the Indian Chemical Society, 1982, vol. 59, # 9, p. 1099 - 1101

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-乙氧基苯基)二硫代氨基甲酸铵 以 丙酮 为溶剂， 反应 3.0h， 生成 6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  Desai; Ravat; Shah, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 367 - 373

  摘要：

  DOI：

文献信息

• An efficient, “green” approach to aryl amination of cyanuric chloride using acetic acid as solvent
  作者：Kirill A. Kolmakov

  DOI：10.1002/jhet.5570450236

  日期：2008.3

  Acetic acid is an inexpensive and environmentally friendly solvent for facile, clean and high-yielding aryl amination of cyanuric chloride with aromatic amines, including nitroanilines. Aryl amination in acetic acid medium and isolation protocol are greatly simplified as compared to previously reported procedures. Under proper conditions, it is possible to attach the same or different aniline residues

  乙酸是一种廉价，环保的溶剂，可用于氰尿酰氯与包括硝基苯胺在内的芳香胺的简便，清洁和高收率的芳基胺化。与以前报道的方法相比，大大简化了乙酸介质中的芳基胺化反应和分离步骤。在适当条件下，可以以受控方式连接相同或不同的苯胺残基，从而分别以优异的产率获得对称和不对称的1,3,5-三嗪衍生物。
• Simple and efficient synthetic routes to bioactive s-triazinyl dithiocarbamate derivatives
  作者：R. M. Desai、D. K. Dodiya、A. R. Trivedi、V. H. Shah

  DOI：10.1007/s00044-008-9093-4

  日期：2008.10

  l]-6-arylamino-s-triazines (7a–l) were synthesized by two different synthetic routes. In the first route (A) , 2,4,6-tricholoro-s-triazine (1) was condensed with N-(3-methylphenyl)ammoniumdithiocarbamate to afford compounds 3 or 6 , which on reaction with different aryl amines afforded compounds 4a–l or 7a–l . In the second route (B) , condensation of 1 with different aryl amines yielded compounds

  2,4-二芳基氨基-6- [N-（3'-甲基苯基）二硫代氨基甲酰基]-三嗪 （4a–l） 和2,4-双[N-（3'-甲基苯基）二硫代氨基甲酰基] -6-系列芳基氨基-s-三嗪 （7a–l） 是通过两种不同的合成途径合成的。在第一途径 （A）中 ，将2,4,6-三氯三嗪 （1） 与N-（3-甲基苯基）二硫代氨基甲酸铵缩合，得到化合物 3 或 6 ，其与不同的芳基胺反应后得到化合物 4a。 –l 或 7a–l 。在第二种方法 （B）中 ， 1 与不同的芳基胺缩合 生成化合物 2a–l 或 5a–l 。进一步用N-（3-甲基苯基）二硫代氨基甲酸铵处理，可制得化合物 4a-1 或 7a-1 。新合成的化合物 4a-1 和 7a-1 通过元素分析，红外（IR）和1 H核磁共振（NMR）光谱学表征。评价所有产品的抗菌和抗真菌活性。
• Design, Facile Synthesis, and Antibacterial Activity of Hybrid 1,3,4-thiadiazole-1,3,5-triazine Derivatives Tethered via -S- Bridge
  作者：Vaibhav Dubey、Manish Pathak、Hans R. Bhat、Udaya P. Singh

  DOI：10.1111/j.1747-0285.2012.01433.x

  日期：2012.10

  Some hybrid 1,3,4‐thiadiazole‐1,3,5‐triazine derivatives tethered via –S– bridge were synthesized and characterized with the aid of spectroscopic and elemental analysis. These hybrid conjugates were then investigated for their antibacterial activity against selected Gram‐positive and Gram‐negative bacteria. Excellent to moderate antibacterial activity was presented by the target compounds.

  合成了一些通过–S–桥束缚的杂合的1,3,4-噻二唑-1,3,5-三嗪衍生物，并借助光谱和元素分析对其进行了表征。然后研究这些杂合缀合物对所选革兰氏阳性和革兰氏阴性细菌的抗菌活性。目标化合物具有极好的中度抗菌活性。
• Design, Facile Synthesis, Antibacterial Activity and Structure-Activity Relationship of Novel Di- and Tri-Substituted 1,3,5-Triazines
  作者：Surajit Kumar Ghosh、Ashmita Saha、Bornali Hazarika、Udaya Pratap Singh、Hans Raj Bhat、Prashant Gahtori

  DOI：10.2174/157018012799129846

  日期：2012.3.1

  continuation of our research on discovery of novel heterocyclic scaffolds from 1,3,5-triazine, present study deals with design and development of some novel di- and tri-substituted 1,3,5-triazine derivatives. The synthesis of title analogues were accomplished by SNAr reaction and subsequently underwent rigorous antibacterial screening against a panel of representative Gram-negative and Gram-positive bacteria

  由于大量产生抗药性微生物，迫切需要开发新型化学治疗剂。在继续我们从1,3,5-三嗪发现新型杂环支架的研究的过程中，本研究涉及一些新型的二和三取代的1,3,5-三嗪衍生物的设计和开发。标题类似物的合成通过SNAr反应完成，然后针对一组代表性的革兰氏阴性和革兰氏阳性细菌进行严格的抗菌筛选。筛选结果表明，微小的结构变异可能会引起活性的急剧变化。胺桥和哌嗪被称为生物活性的产生和升级所必需的关键结构片段。
• 4-Aminoquinoline-1,3,5-triazine: Design, synthesis, in vitro antimalarial activity and docking studies
  作者：Hans Raj Bhat、Udaya Pratap Singh、Prashant Gahtori、Surajit Kumar Ghosh、Kabita Gogoi、Anil Prakash、Ramendra K. Singh

  DOI：10.1039/c3nj00317e

  日期：——

  A series of hybrid 4-aminoquinoline 1,3,5-triazine derivatives was synthesized and their chemical structure were confirmed by 1H-NMR, 13C-NMR, FT-IR and mass spectrometric analyses. In vitro antimalarial activity of these compounds was evaluated against chloroquine-sensitive (3D-7) and chloroquine resistant (RKL-2) strains of P. falciparum. Results showed that all compounds had considerable antimalarial activity against both the strains and further docking studies were performed on both wild type (1J3I.pdb) and quadruple mutant (N51I, C59R, S108 N, I164L, 3QG2.pdb) pf-DHFR-TS to quantify the structural parameter necessary for the activity.

  合成了一系列 4-氨基喹啉-1,3,5-三嗪杂化衍生物，并通过 1H-NMR、13C-NMR、FT-IR 和质谱分析确认了它们的化学结构。评估了这些化合物对氯喹敏感菌株（3D-7）和对氯喹耐药菌株（RKL-2）的体外抗疟活性。结果表明，所有化合物对这两种菌株都具有相当高的抗疟活性，并对野生型（1J3I.pdb）和四重突变型（N51I、C59R、S108 N、I164L、3QG2.pdb）pf-DHFR-TS 进行了进一步的对接研究，以量化活性所需的结构参数。