4-azido-2-methoxyphenol | 1268445-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-azido-2-methoxyphenol
• CAS: 1268445-26-6
• 化学式: C₇H₇N₃O₂
• 分子量: 165.151
• InChiKey: OYWRVVSTNSTBPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-azido-2-methoxyphenol 在 copper(l) iodide 、 铁粉 、 氯化铵 、 caesium carbonate 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-(1-(3-methoxy-4-(2-morpholinoethoxy)phenyl)-1H-1,2,3-triazol-4-yl)phenyl)urea
  参考文献：
  名称：

  Identification and Development of 1,4-Diaryl-1,2,3-triazolo-Based Ureas as Novel FLT3 Inhibitors

  摘要：

  A class were of 1,4-diaryl-1,2,3-triazolo-based ureas were synthesized and developed as novel FLT3 inhibitors. The representative compound 28 strongly inhibited FLT3-ITD kinase (IC50 = 32.8 nM) and isogenic BaF3-FLT3-ITD cell (GI(50) = 0.6 nM). It exhibited potent inhibition against FLT3-ITD positive MV4-11 (GI(50) = 3.0 nM) and MOLM-13 (GI(50) = 5.9 nM) cell lines and high selectivity over FLT3-WT cell lines. It also displayed good pharmacokinetics properties and demonstrated promising oral in vivo efficacy in a MV4-11 cell xenografted mouse model. It might be a potent lead compound for further development to treat FLT3-ITD driven acute myloid leukemia.

  DOI：

  10.1021/acsmedchemlett.0c00216

文献信息

• Photochemical C-H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D
  作者：Isak Alimi、Richard Remy、Christian G. Bochet

  DOI：10.1002/ejoc.201700300

  日期：2017.6.16

  N-arylbenzotriazoles leads respectively to indoles and carbazoles. Because the very rapid access to libraries of triazoles, for example by the copper-catalyzed [3+2] cycloaddition between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first

  N-芳基三唑和N-芳基苯并三唑的光解分别导致吲哚和咔唑。因为可以非常快速地访问三唑库，例如通过炔烃和叠氮化物之间的铜催化 [3+2] 环加成反应，该反应允许通过同时光解前体库，在单次操作中制备吲哚。作为咔唑类合成的一个例子，我们首次制备了 Clausenawalline D，这是一种最近分离的抗疟生物碱。
• Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation
  作者：Ornella Mesenzani、Alberto Massarotti、Mariateresa Giustiniano、Tracey Pirali、Valentina Bevilacqua、Antonio Caldarelli、Pierluigi Canonico、Giovanni Sorba、Ettore Novellino、Armando A. Genazzani、Gian Cesare Tron

  DOI：10.1016/j.bmcl.2010.11.113

  日期：2011.1

  In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker. (C) 2010 Elsevier Ltd. All rights reserved.