(3-Chloro-4-fluoro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine | 1174140-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Chloro-4-fluoro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine
• 英文别名: 4,6-dichloro-N-(3-chloro-4-fluorophenyl)-1,3,5-triazin-2-amine
• CAS: 1174140-78-3
• 化学式: C₉H₄Cl₃FN₄
• 分子量: 293.515
• InChiKey: NIUJLRNDNGJQIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-Chloro-4-fluoro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine 在 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-(4-(p-toluidino)-6-(3-chloro-4-fluorophenylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)nicotinonitrile
  参考文献：
  名称：

  Development of cyanopyridine–triazine hybrids as lead multitarget anti-Alzheimer agents

  摘要：

  A series of new cyanopyridine-triazine hybrids were designed, synthesized and screened as multitargeted anti-Alzheimer's agents. These molecules were designed while using computational techniques and were synthesized via a feasible concurrent synthetic route. Inhibition potencies of synthetic compounds 4a-4h against cholinesterases, A beta(1-42) disaggregation, oxidative stress, cytotoxicity, and neuroprotection against A beta(1-42)-induced toxicity of the synthesized compounds were evaluated. Compounds 4d and 4h showed promising inhibitory activity on acetylcholinesterase (AChE) with IC50 values 0.059 and 0.080 mu M, respectively, along with good inhibition selectivity against AChE over butyrylcholinesterase (BuChE). Molecular modelling studies revealed that these compounds interacted simultaneously with the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. The mixed type inhibition of compound 4d further confirmed their dual binding nature in kinetic studies. Furthermore, the results from neuroprotection studies of most potent compounds 4d and 4h indicate that these derivatives can reduce neuronal death induced by H2O2-mediated oxidative stress and A beta(1-42) induced cytotoxicity. In addition, in silico analysis of absorption, distribution, metabolism and excretion (ADME) profile of best compounds 4d and 4h revealed that they have drug like properties. Overall, these cyanopyridine-triazine hybrids can be considered as a candidate with potential impact for further pharmacological development in Alzheimer's therapy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.041
• 作为产物：
  描述：

  三聚氯氰 、 3-氯-4-氟苯胺 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (3-Chloro-4-fluoro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine
  参考文献：
  名称：

  Synthesis and In Vitro Antibacterial Screening of some New 2,4,6-Trisubstituted-1,3,5-Triazine Derivatives

  摘要：

  为了评估三嗪衍生物的抗菌活性，合成并表征了一系列2,4,6-三取代-1,3,5-三嗪化合物，包括FTIR、1H-NMR、13C-NMR、质谱和元素分析。通过肉汤微量稀释法测定了显示出良好抑制圈的化合物的最小抑制浓度（MIC）。具有吗啉基取代基的衍生物（4a和4i）对革兰氏阳性菌显示出良好的体外活性，而具有二乙氨基侧链的两个化合物显示出中等（4e）至广谱（4j）活性，可与链霉素相媲美。后者的潜在活性可能归因于苯环对位上电子给体基团的取代。

  DOI：

  10.2174/157018012799129936

文献信息

• Rational design, synthesis and biological screening of triazine-triazolopyrimidine hybrids as multitarget anti-Alzheimer agents
  作者：Ehtesham Jameel、Poonam Meena、Mudasir Maqbool、Jitendra Kumar、Waqar Ahmed、Syed Mumtazuddin、Manisha Tiwari、Nasimul Hoda、B. Jayaram

  DOI：10.1016/j.ejmech.2017.04.064

  日期：2017.8

  AChE. In addition, these derivatives effectively modulated Aβ self-aggregation as investigated through CD spectroscopy, ThT fluorescence assay and electron microscopy. Besides, these compounds exhibited potential antioxidants (2.15 and 2.91 trolox equivalent by ORAC assay) and metal chelating properties. In silico ADMET profiling highlighted that, these novel triazine derivatives have appropriate drug

  为了开发用于治疗阿尔茨海默氏病的有效多靶点配体，我们通过各种光谱技术设计，合成和表征了一系列三嗪-三唑并嘧啶杂化物。用对接和评分技术设计抑制剂并显示其与活性位点关键残基的相互作用。依靠会聚合成路线的有机合成是单和二取代的三嗪与三唑并嘧啶连接，并使用哌嗪作为连接基。总共合成了十七种化合物，其中二取代的三嗪-三唑并嘧啶衍生物9a-d显示出比相应的三取代的三嗪-三唑并嘧啶衍生物更好的乙酰胆碱酯酶（AChE）抑制活性。在基于二取代三嗪-三唑并嘧啶的化合物中，9a和9b对AChE表现出令人鼓舞的抑制活性，IC50值分别为0.065和0.092μM。有趣的是，9a和9b对AChE的抑制选择性也比BuChE高约28倍。此外，动力学分析和分子建模研究表明9a和9b既靶向AChE的催化活性位点，又靶向其外围阴离子位点。此外，如通过CD光谱，ThT荧光测定和电子显微镜研究的，这些衍生物有效地调节了Aβ的自聚集
• Triazines And Related Compounds Having Antiviral Activity, Compositions And Methods Thereof
  申请人：Han Amy Qi

  公开号：US20120009151A1

  公开（公告）日：2012-01-12

  Disclosed herein are novel triazines and related compounds, the synthesis thereof, and compositions, including pharmaceutical compositions, comprising the novel triazines and related compounds. Such novel triazines and related compounds function to inhibit or block entry of viruses of the Flaviviridae family, including Hepatitis C virus (HCV), into cells that are susceptible to virus infection. These compounds are useful for the treatment, therapy and/or prophylaxis of viral diseases and infection, including HCV infection.

  本文披露了新型三嗪及其相关化合物，其合成方法以及包含新型三嗪和相关化合物的组合物，包括药物组合物。这些新型三嗪和相关化合物的功能是抑制或阻止易感染病毒的细胞进入黄病毒科病毒，包括丙型肝炎病毒（HCV）。这些化合物对于治疗、治疗和/或预防病毒性疾病和感染，包括HCV感染，是有用的。
• TRIAZINES AND RELATED COMPOUNDS HAVING ANTIVIRAL ACTIVITY, COMPOSITIONS AND METHODS THEREOF
  申请人：Progenics Pharmaceuticals, Inc.

  公开号：EP2231624A2

  公开（公告）日：2010-09-29
• [EN] TRIAZINES AND RELATED COMPOUNDS HAVING ANTIVIRAL ACTIVITY, COMPOSITIONS AND METHODS THEREOF<br/>[FR] TRIAZINES ET COMPOSÉS ASSOCIÉS PRÉSENTANT UNE ACTIVITÉ ANTIVIRALE, COMPOSITIONS ET PROCÉDÉS ASSOCIÉS
  申请人：PROGENICS PHARM INC

  公开号：WO2009091388A2

  公开（公告）日：2009-07-23

  Disclosed herein are novel triazines and related compounds, the synthesis thereof, and compositions, including pharmaceutical compositions, comprising the novel triazines and related compounds. Such novel triazines and related compounds function to inhibit or block entry of viruses of the Flaviviridae family, including Hepatitis C virus (HCV), into cells that are susceptible to virus infection. These compounds are useful for the treatment, therapy and/or prophylaxis of viral diseases and infection, including HCV infection.