N²,N⁴-bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine | 62785-05-1

• 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,N⁴-bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine
• 英文别名: N~2~,N~4~-Bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine；2-N,4-N-bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine
• CAS: 62785-05-1
• 化学式: C₁₅H₁₀Br₂ClN₅
• 分子量: 455.539
• InChiKey: MAZDADAVYCVEEV-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C(Solv: ethanol (64-17-5))
• 沸点：
  582.1±60.0 °C(Predicted)
• 密度：
  1.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N²,N⁴-bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 18.0h， 生成 4-(4,6-bis(4-bromophenylamino)-1,3,5-triazin-2-yl)-N-(7-chloroquinolin-4-yl)piperazine-1-carbothioamide
  参考文献：
  名称：

  Antimalarial activity and docking studies of novel bi-functional hybrids derived from 4-aminoquinoline and 1,3,5-triazine against wild and mutant malaria parasites as pf-DHFR inhibitor

  摘要：

  通过简便的合成路线合成了由 4-氨基喹啉和 1,3,5-三嗪组成的双功能共轭物。对这些化合物进行了严格筛选，以确定它们对野生和变异培养的恶性疟原虫的抗疟活性。结果表明，这些共轭物对野生寄生虫和变异寄生虫都具有相当强的抗疟活性，而且随着取代模式的改变而发生明显变化。此外，对野生和四重突变的恶性疟原虫二氢叶酸还原酶胸苷酸合成酶（pf-DHFR-TS）进行的对接研究也证实了观察到的活性特征。

  DOI：

  10.1039/c2ra21915h
• 作为产物：
  描述：

  4-溴苯胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N²,N⁴-bis(4-bromophenyl)-6-chloro-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Triaminotriazine DNA helicase inhibitors with antibacterial activity

  摘要：

  Screening of a chemical library in a DNA helicase assay involving the Pseudomonas aeruginosa DnaB helicase provided a triaminotriazine inhibitor with good antibacterial activity but associated cytotoxicity toward mammalian cells. Synthesis of analogs provided a few inhibitors that retained antibacterial activity and demonstrated a significant reduction in cytotoxicity. The impact of serum and initial investigations toward a mode of action highlight several features of this class of compounds as antibacterials. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.076

文献信息

• 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。
• Discovery of novel 1,3,5-triazine-thiazolidine-2,4-diones as dipeptidyl peptidase-4 inhibitors with antibacterial activity targeting the S1 pocket for the treatment of type 2 diabetes
  作者：Jitendra Kumar Srivastava、Pragya Dubey、Saumya Singh、Hans Raj Bhat、Mukesh Kumar Kumawat、Udaya Pratap Singh

  DOI：10.1039/c4ra16903d

  日期：——

  A novel series of 1,3,5-triazine-thiazolidine-2,4-diones was synthesized and characterized by a number of analytical and spectroscopic techniques.

  合成并通过多种分析和光谱技术表征了一系列1,3,5-三嗪-噻唑啉-2,4-二酮的新颖系列。
• 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。
• Synthesis and antibacterial evaluation of series of novel tri-substituted-s-triazine derivatives
  作者：Udaya Pratap Singh、Ramendra Kumar Singh、Hans Raj Bhat、Yadav Pankajkumar Subhashchandra、Vikas Kumar、Mukesh Kumar Kumawat、Prashant Gahtori

  DOI：10.1007/s00044-010-9446-7

  日期：2011.12

  Two novel series of s-triazine derivatives (6a-e and 7a-f) were synthesized with various aromatic and heterocyclic amines. The synthesized compounds were subsequently evaluated for their in vitro antibacterial activity against three gram-positive viz. Bacillus subtilis (NCIM-2063), Bacillus cereus (NCIM-2156), Staphylococcus aureus (NCIM-2079) and gram-negative bacteria viz. Pseudomonas aeruginosa (NCIM-2036), Escherichia coli (NCIM-2065) and Klebseilla pneumoniae (NCIM-2706) by the broth dilution method as recommended by the National Committee for Clinical Laboratory Standards (NCCLS) using streptomycin as reference standard. Structures of the synthesized compounds were elucidated on the basis of elemental analyses and spectral data.
• Mehta, Lina; Parekh, Hansa, Journal of the Indian Chemical Society, 1986, vol. 63, p. 414 - 416
  作者：Mehta, Lina、Parekh, Hansa

  DOI：——

  日期：——