2,4-dichloro-6-cyclohexyl-1,3,5-triazine | 17419-41-9

• 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: 2,4-dichloro-6-cyclohexyl-1,3,5-triazine
• CAS: 17419-41-9
• 化学式: C₉H₁₁Cl₂N₃
• 分子量: 232.112
• InChiKey: RNUNMDBBXRZXFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-cyclohexyl-1,3,5-triazine 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  发现新型三嗪衍生物作为有效的视黄酸受体相关孤儿受体 γt (RORγt) 反向激动剂

  摘要：

  视黄酸受体相关孤儿受体 γt (RORγt) 已被用作新的小分子疗法的有希望的靶标，通过调节 T 辅助细胞 17 (Th17) 细胞产生的白细胞介素 17 (IL-17) 来治疗炎症和自身免疫性疾病. 在此，我们报道了一系列基于三嗪的衍生物作为新型 RORγt 反向激动剂。通过筛选我们的内部化合物库，发现命中化合物1具有较弱的 RORγt 抑制活性。随后，我们设计了详细的结构修饰以探索三嗪衍生物的构效关系 (SAR)，从而发现了许多有效的 RORγt 反向激动剂，在 RORγt 双 FRET 中的 IC 50 值范围为 7 nM– 50 nM化验。其中，复方14g在双 FRET 测定中显示出有效的 RORγt 反向激动活性，IC 50值为 22.9 nM。在基于细胞的报告基因测定中，化合物14g显示出 0.428 μM 的 IC 50值和 108.9% 的最大抑制率。化合物14g还表现出良

  DOI：

  10.1016/j.ejmech.2023.115424
• 作为产物：
  描述：

  三聚氯氰 、 环己氯化镁 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 以36%的产率得到2,4-dichloro-6-cyclohexyl-1,3,5-triazine
  参考文献：
  名称：

  格氏反应的标记组合三嗪文库的新型正交合成

  摘要：

  为了通过CC键扩展1,3,5-三嗪库到芳基和烷基官能团的多样性，我们采用了通过溶液中氰尿酰氯的格利雅德单烷基化或单芳基化的新型正交合成方法制备芳基或烷基取代的三嗪建筑模块。这些芳基或烷基取代的三嗪结构单元被树脂结合的胺捕获，然后进行胺化和高纯度的酸性裂解。在这里，我们展示了利用固溶体通过格氏反应制备的结构单元，在固相支持物上标记的芳基和烷基三嗪库的新型正交合成方法。通过在三嗪支架上的替代位点之一处引入三甘醇接头，我们探索了一种内在的标签文库方法。

  DOI：

  10.1071/ch09153

文献信息

• New free-radical chain processes involving substitution of vinyl and aryl chlorides by alkanes, alkenes, esters and ethers
  作者：Silvia Araneo、Riccardo Arrigoni、Hans-René Bjørsvik、Francesca Fontana、Lucia Liguori、Francesco Minisci、Francesco Recupero

  DOI：10.1016/0040-4039(96)01510-9

  日期：1996.9

  New free-radical substitutions of vinyl and aryl chlorides by alkanes, alkenes, ethers and esters are described. The free-radical chains are rationalized on the basis of the known kinetics of the elementary steps involved.

  描述了用烷烃，烯烃，醚和酯对乙烯基氯和芳基氯进行的新的自由基取代。自由基链根据所涉及的基本步骤的已知动力学而合理化。
• Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction
  作者：Jae Wook Lee、Jacqueline T. Bork、Hyung-Ho Ha、Animesh Samanta、Young-Tae Chang

  DOI：10.1071/ch09153

  日期：——

  To expand the diversity of 1,3,5-triazine libraries to aryl and alkyl functionalities through the C–C bond, we employed a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution to prepare aryl- or alkyl-substituted triazine building blocks. These aryl- or alkyl-substituted triazine building blocks were captured by a resin-bound amine, followed by amination

  为了通过CC键扩展1,3,5-三嗪库到芳基和烷基官能团的多样性，我们采用了通过溶液中氰尿酰氯的格利雅德单烷基化或单芳基化的新型正交合成方法制备芳基或烷基取代的三嗪建筑模块。这些芳基或烷基取代的三嗪结构单元被树脂结合的胺捕获，然后进行胺化和高纯度的酸性裂解。在这里，我们展示了利用固溶体通过格氏反应制备的结构单元，在固相支持物上标记的芳基和烷基三嗪库的新型正交合成方法。通过在三嗪支架上的替代位点之一处引入三甘醇接头，我们探索了一种内在的标签文库方法。
• Discovery of 1-(1,3,5-triazin-2-yl)piperidine-4-carboxamides as inhibitors of soluble epoxide hydrolase
  作者：Reema K. Thalji、Jeff J. McAtee、Svetlana Belyanskaya、Martin Brandt、Gregory D. Brown、Melissa H. Costell、Yun Ding、Jason W. Dodson、Steve H. Eisennagel、Rusty E. Fries、Jeffrey W. Gross、Mark R. Harpel、Dennis A. Holt、David I. Israel、Larry J. Jolivette、Daniel Krosky、Hu Li、Quinn Lu、Tracy Mandichak、Theresa Roethke、Christine G. Schnackenberg、Benjamin Schwartz、Lisa M. Shewchuk、Wensheng Xie、David J. Behm、Stephen A. Douglas、Ami L. Shaw、Joseph P. Marino

  DOI：10.1016/j.bmcl.2013.04.019

  日期：2013.6

  1-(1,3,5-Triazin-yl)piperidine-4-carboxamide inhibitors of soluble epoxide hydrolase were identified from high through-put screening using encoded library technology. The triazine heterocycle proved to be a critical functional group, essential for high potency and P450 selectivity. Phenyl group substitution was important for reducing clearance, and establishing good oral exposure. Based on this lead optimization work, 1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-N-[[4-bromo-2-(trifluoromethoxy)]-phenyl]methyl}-4-piperidinecarboxamide (27) was identified as a useful tool compound for in vivo investigation. Robust effects on a serum biomarker, 9, 10-epoxyoctadec-12(Z)-enoic acid (the epoxide derived from linoleic acid) were observed, which provided evidence of robust in vivo target engagement and the suitability of 27 as a tool compound for study in various disease models. Published by Elsevier Ltd.
• Combinatorial Solid-Phase Synthesis of 4,6-Diaryl and 4-Aryl, 6-Alkyl-1,3,5-triazines and Their Application to Efficient Biofuel Production
  作者：Jaoon Y. H. Kim、Jae Wook Lee、Woo Sirl Lee、Hyung-Ho Ha、Marc Vendrell、Jacqueline T. Bork、Youngsook Lee、Young-Tae Chang

  DOI：10.1021/co300007a

  日期：2012.7.9

  Herein we report the solid-phase synthesis of a combinatorial aryl, alkyl-triazine library and its application to biofuel production. The combination of Grignard reactions and solid supported Suzuki coupling reactions afforded unique 120 triazine compounds with high purities and minimum purification steps. Through an unbiased phenotypic screening for improved biofuel generation in oleaginous yeast, we found one diaryl triazine derivative (E4) which increased the biolipid production up to 86%.
• Synthesis and biological evaluation of novel 1,3,5-triazine derivatives as antimicrobial agents
  作者：Chunhui Zhou、Jaeki Min、Zhigang Liu、Anne Young、Heather Deshazer、Tian Gao、Young-Tae Chang、Neville R. Kallenbach

  DOI：10.1016/j.bmcl.2008.01.031

  日期：2008.2

  Numerous studies have contributed to the development of natural and synthetic antimicrobial peptides as a prospective source of antibiotic agents. Based on the concept that cationic charge, bulk, and lipophilicity are major factors determining antibacterial activity in these peptides, we designed and screened several combinatorial libraries based on 1,3,5-triazine as a template. A set of compounds were identified to show potent antimicrobial activity together with low hemolytic activity. (c) 2008 Elsevier Ltd. All rights reserved.