2-azido-1-(6-methoxynaphthalen-2-yl)ethanone | 1001422-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-azido-1-(6-methoxynaphthalen-2-yl)ethanone
• 英文别名: 2-azido-1-(6-methoxynaphthalen-2-yl)ethan-1-one
• CAS: 1001422-37-2
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: BBEDMISNSGCMDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-1-(6-methoxynaphthalen-2-yl)ethanone 、 4-(ethylsulfonyl)-2-isothiocyanato-1-methoxybenzene 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以30%的产率得到N-(5-(ethylsulfonyl)-2-methoxyphenyl)-5-(6-methoxynaphthalen-2-yl)oxazol-2-amine
  参考文献：
  名称：

  Novel CLK1 inhibitors based on N-aryloxazol-2-amine skeleton - A possible way to dual VEGFR2 TK/CLK ligands

  摘要：

  Background: Inhibitors of CLK protein kinases suppress cell growth and induce apoptosis by modulating pre-mRNA splicing in cancer. CLK family kinases are also involved in alternative splicing and RNA processing in Duchenne muscular dystrophy, Alzheimer's disease, HIV-1, and influenza virus. Small inhibitors are valuable tools for better understanding the molecular mechanisms of splicing and may serve as seeds for a novel class of therapeutics.Achievements: Here we describe a discovery of four novel CLK1 inhibitors possessing N-aryloxazol-2amine skeleton. Their activity against CLK1 (IC50: 20, 30, 40 and 80 nM) and some other CMGC kinases, predicted CLK binding poses, synthesis and physico-chemical characteristics are also stated. Additionally analysis of all PDB available CLK structures and interactions of their ligands was performed. There are only few powerful dual CLK/VEGFR inhibitors known in the literature. We proposed that our inhibitors have similar binding places and interactions in CLK1, 3 and VEGFR2 TK mostly due to the joint N-aryloxazol-2-amine pharmacophoric fragment. One of our N-aryloxazol-2-amines already proved a good activity against both VEGFR2 and CLK1 enzymes (23/80 nM, resp). We, proposed that the presented class of compounds has a potential to be developed in dual VEGFR2/CLK clinical compounds with prospective synergy to treat cancer. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.003
• 作为产物：
  描述：

  6-甲氧基-2-乙酰萘 在 sodium azide 、 oxone 、 溴化铵 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 2-azido-1-(6-methoxynaphthalen-2-yl)ethanone
  参考文献：
  名称：

  松萝酸烯胺酮偶联的1,2,3-三唑类用作抗菌剂和抗结核剂。

  摘要：

  （+）-尿酸是地衣中的二次代谢产物，具有广泛的生物学特性，例如抗肿瘤，抗微生物，抗病毒，抗炎和杀虫活性。对这些药理活性感兴趣并挖掘其潜力，我们在此介绍新的松萝酸烯胺酮偶联的1,2,3-三唑10-44作为抗分枝杆菌药的合成和生物学评估。将（+）-松香酸与炔丙基胺缩合，得到具有末端乙炔基部分的松香酸烯胺酮8。在铜催化下，它进一步与各种叠氮化物A1-A35反应，以高收率得到三唑10-44。在合成的化合物中，糖精衍生物36被证明是活性最高的类似物，在MIC值为2.5μM时可抑制结核分枝杆菌（Mtb）。类似物16和27，以及3，4-二氟苯酰基和2-酰基萘单元分别在MIC值为5.4和5.3μM时抑制Mtb。在测试的革兰氏阳性和革兰氏阴性细菌中，新衍生物对枯草芽孢杆菌具有活性，化合物18 [3-（三氟甲基）苯甲酰基]和29（N-酰基吗啉基）分别显示抑制浓度41和90.7μM，而它们对其他测试细菌菌株没有

  DOI：

  10.1021/acs.jnatprod.9b00475

文献信息

• A NOVEL ACCESS TO SOME 1,4-DICHLOROISOQUINOLINES FROM PHENACYL AZIDES
  作者：R. E. Chen、X. H. Zhou、W. H. Zhong、W. K. Su

  DOI：10.1080/00304940809458125

  日期：2008.12

  such as quinolines, indoles, quinazolines, pyridines, etc. In continuation of our previous work on exploring the use of bis(trichloromethy1) carbonate (BTC) in organic synthesis: we focused our research on the use of Vilsmeier salts derived from BTC and N,N-dimethylfomamide (DMF).5 Herein we describe a mild and efficient one-step synthesis of substituted 1,4-dichloroisoquinolines and 5-aryloxazole-4-carboxaldehydes

  最初用于活化芳香底物和羰基化合物 2 的甲酰化的 Vilsmeier-Haack 反应现已发展成为构建许多杂环化合物 3 如喹啉、吲哚、喹唑啉、吡啶等的强大合成工具。探索在有机合成中使用双（三氯甲基）碳酸酯 (BTC) 的工作：我们的研究重点是使用衍生自 BTC 和 N,N-二甲基甲酰胺 (DMF) 的 Vilsmeier 盐。 5 在此我们描述了一种温和高效的盐在 Vilsmeier 条件下从各种苯甲酰叠氮化物逐步合成取代的 1,4-二氯异喹啉和 5-芳基恶唑-4-甲醛。
• Electrochemical Aerobic Oxygenation and Nitrogenation of Cyclic Alkenes via C═C Bond Cleavage or Oxygenation and Azidation of Open-Chain Alkenes
  作者：Yan Zhu、Cong Jiang、Heng Li、Ping Liu、Peipei Sun

  DOI：10.1021/acs.joc.2c01293

  日期：2022.8.19

  electrochemical C═C double-bond cleavage and functionalization of cyclic alkenes for the synthesis of ketonitriles is described. This transformation features environmentally friendly conditions and utilizes relatively safe TMSN3 as the nitrogenation reagent and molecular oxygen as the oxidant. For the open-chain alkenes, the reaction gave 1,2-difunctionalized products. A wide range of cyclic alkenes and open-chain

  描述了一种涉及电化学 C=C 双键裂解和环状烯烃功能化合成酮腈的有效策略。这种转化具有环境友好的条件，并使用相对安全的TMSN 3作为氮化试剂和分子氧作为氧化剂。对于开链烯烃，反应产生 1,2-双官能化产物。发现多种环状烯烃和开链烯烃是相容的，以中等至良好的产率提供相应的酮腈和 α-叠氮基芳族酮。
• Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents
  作者：Pavan K. Bangalore、Siva K. Vagolu、Rakesh K. Bollikanda、Dileep K. Veeragoni、Pallavi C. Choudante、Sunil Misra、Dharmarajan Sriram、Balasubramanian Sridhar、Srinivas Kantevari

  DOI：10.1021/acs.jnatprod.9b00475

  日期：2020.1.24

  be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl]

  （+）-尿酸是地衣中的二次代谢产物，具有广泛的生物学特性，例如抗肿瘤，抗微生物，抗病毒，抗炎和杀虫活性。对这些药理活性感兴趣并挖掘其潜力，我们在此介绍新的松萝酸烯胺酮偶联的1,2,3-三唑10-44作为抗分枝杆菌药的合成和生物学评估。将（+）-松香酸与炔丙基胺缩合，得到具有末端乙炔基部分的松香酸烯胺酮8。在铜催化下，它进一步与各种叠氮化物A1-A35反应，以高收率得到三唑10-44。在合成的化合物中，糖精衍生物36被证明是活性最高的类似物，在MIC值为2.5μM时可抑制结核分枝杆菌（Mtb）。类似物16和27，以及3，4-二氟苯酰基和2-酰基萘单元分别在MIC值为5.4和5.3μM时抑制Mtb。在测试的革兰氏阳性和革兰氏阴性细菌中，新衍生物对枯草芽孢杆菌具有活性，化合物18 [3-（三氟甲基）苯甲酰基]和29（N-酰基吗啉基）分别显示抑制浓度41和90.7μM，而它们对其他测试细菌菌株没有
• Novel CLK1 inhibitors based on N-aryloxazol-2-amine skeleton - A possible way to dual VEGFR2 TK/CLK ligands
  作者：Miroslav Murár、Juraj Dobiaš、Peter Šramel、Gabriela Addová、Gilles Hanquet、Andrej Boháč

  DOI：10.1016/j.ejmech.2016.11.003

  日期：2017.1

  Background: Inhibitors of CLK protein kinases suppress cell growth and induce apoptosis by modulating pre-mRNA splicing in cancer. CLK family kinases are also involved in alternative splicing and RNA processing in Duchenne muscular dystrophy, Alzheimer's disease, HIV-1, and influenza virus. Small inhibitors are valuable tools for better understanding the molecular mechanisms of splicing and may serve as seeds for a novel class of therapeutics.Achievements: Here we describe a discovery of four novel CLK1 inhibitors possessing N-aryloxazol-2amine skeleton. Their activity against CLK1 (IC50: 20, 30, 40 and 80 nM) and some other CMGC kinases, predicted CLK binding poses, synthesis and physico-chemical characteristics are also stated. Additionally analysis of all PDB available CLK structures and interactions of their ligands was performed. There are only few powerful dual CLK/VEGFR inhibitors known in the literature. We proposed that our inhibitors have similar binding places and interactions in CLK1, 3 and VEGFR2 TK mostly due to the joint N-aryloxazol-2-amine pharmacophoric fragment. One of our N-aryloxazol-2-amines already proved a good activity against both VEGFR2 and CLK1 enzymes (23/80 nM, resp). We, proposed that the presented class of compounds has a potential to be developed in dual VEGFR2/CLK clinical compounds with prospective synergy to treat cancer. (C) 2016 Elsevier Masson SAS. All rights reserved.