6-(p-hydroxyanilino)-1,3,5-triazine-2,4-dichloride | 46731-78-6

• 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: 6-(p-hydroxyanilino)-1,3,5-triazine-2,4-dichloride
• 英文别名: 4-(4,6-dichloro-1,3,5-triazin-2-ylamino)phenol；2-(4-hydroxy-phenylamino)-4,6-dichloro-[1,3,5]triazine；4-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]phenol
• CAS: 46731-78-6
• 化学式: C₉H₆Cl₂N₄O
• 分子量: 257.079
• InChiKey: AADGRYXZNWPRCG-UHFFFAOYSA-N

物化性质

• 沸点：
  514.7±52.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 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：
  70.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(p-hydroxyanilino)-1,3,5-triazine-2,4-dichloride 在 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 4,4'-(6-(piperazin-1-yl)-1,3,5-triazine-2,4-diyl)bis(azanediyl)diphenol
  参考文献：
  名称：

  二，三取代的1,3,5-三嗪的设计，合成，抗菌活性及构效关系

  摘要：

  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。

  DOI：

  10.2174/157018012799129846
• 作为产物：
  描述：

  三聚氯氰 、 对氨基苯酚 以 四氢呋喃 为溶剂， 生成 6-(p-hydroxyanilino)-1,3,5-triazine-2,4-dichloride
  参考文献：
  名称：

  二，三取代的1,3,5-三嗪的设计，合成，抗菌活性及构效关系

  摘要：

  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。

  DOI：

  10.2174/157018012799129846

文献信息

• Design and development of novel thiazolidin‐4‐one‐1,3,5‐triazine derivatives as neuro‐protective agent against cerebral ischemia–reperfusion injury in mice <i>via</i> attenuation of NF‐ĸB
  作者：Min Lu、Yujun Qi、Yu Han、Qiong Yi、Lei Xu、Wenlin Sun、Guihua Ni、Xiaoyu Ni、Changsong Xu

  DOI：10.1111/cbdd.13744

  日期：2020.11

  enumerates the discovery and development of novel thiazolidin‐4‐one‐1,3,5‐triazine as neuro‐protective agent against cerebral ischemia–reperfusion injury in mice. These compounds showed significant inhibition of NF‐ĸB transcriptional activity in LPS‐stimulated RAW264.7 cells, displaying compound 8k as most potent inhibitor among the tested derivative. The compound 8k was further studied in in vivo middle cerebral

  本研究列举了新型噻唑烷-4-one-1,3,5-三嗪作为小鼠脑缺血再灌注损伤的神经保护剂的发现和开发。这些化合物在 LPS 刺激的 RAW264.7 细胞中显示出对 NF-ĸB 转录活性的显着抑制，显示化合物8k是测试衍生物中最有效的抑制剂。在体内大脑中动脉闭塞 (MCAO) 小鼠模型中进一步研究了化合物8k 的神经保护作用。结果表明，化合物8k在 MCAO 小鼠中引起炎症（TNF-α、IL-β 和 IL-6）、氧化应激（SOD、GSH 和 MDA）和细胞凋亡（Bcl-2、Bax 和裂解的 caspase-3）的减弱依赖方式。总的来说，我们的结果证明化合物8k预处理可以保护脑 I/R。这种新型铅支架可能有助于通过灭活 NF-ĸB 来研究新的神经保护剂。
• 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。
• Targeting the hydrophobic region of Hsp90’s ATP binding pocket with novel 1,3,5-triazines
  作者：Taeho Lee、Young Ho Seo

  DOI：10.1016/j.bmcl.2013.09.050

  日期：2013.12

  Heat shock protein 90 (Hsp90) is a molecular chaperone that plays an important role in regulating the maturation and stabilization of many oncogenic proteins. In an attempt to discover a new class of Hsp90 inhibitors, a series of 1,3,5-triazine compounds were rationally designed, synthesized, and their biological activities were evaluated. Compound 3b was found to degrade Hsp90's client proteins of Her2, Met and Akt and to induce the expression level of Hsp70. The binding mode of 3b in the ATP-binding site of Hsp90 was predicted by the molecular docking. (C) 2013 Elsevier Ltd. All rights reserved.
• Tailoring the Substitution Pattern on 1,3,5-Triazine for Targeting Cyclooxygenase-2: Discovery and Structure–Activity Relationship of Triazine–4-Aminophenylmorpholin-3-one Hybrids that Reverse Algesia and Inflammation in Swiss Albino Mice
  作者：Palwinder Singh、Sukhmeet Kaur、Priya Kumari、Baljit Kaur、Manpreet Kaur、Gurjit Singh、Rajbir Bhatti、Manpreet Bhatti

  DOI：10.1021/acs.jmedchem.8b00922

  日期：2018.9.13

  Here, we report analgesic and anti-inflammatory activity of a series of compounds obtained by appending 4-aminophenylmorpholin-3-one and acyclic, cyclic, or hetero-cyclic moieties on 1,3,5-triazine. The structures of compounds 4b and 6b are optimized for the best inhibition of COX-2 with IC50 values of 0.06 and 0.08 mu M, respectively, and selectivity over COX-1 of 166 and >125, respectively. At the dose of 5 mg kg(-1), these compounds significantly reduced acetic acid induced writhings, and their ED50 values were found to be 2.2 and 1.9 mg kg(-1), respectively. Besides the cell-based and animal-based experiments showing the modes of action of these compounds targeting COX-2, the interaction behavior of 4b with COX-2 was also characterized, with physicochemical experiments including ITC, NMR, UV-vis, and molecular-modeling studies. Characteristically, these compounds interact with R120, Y355, and W385, the residues responsible for holding the substrate and mediating the process of electron transfer during the metabolic phase of the enzyme.
• [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：WO2009091388A4

  公开（公告）日：2009-12-23