N-prop-2-yn-1-ylquinolin-6-amine | 1343774-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-prop-2-yn-1-ylquinolin-6-amine
• 英文别名: N-prop-2-ynylquinolin-6-amine
• CAS: 1343774-35-5
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: BSYBRYXXOMXFPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-prop-2-yn-1-ylquinolin-6-amine 、 在 copper(I) iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以88%的产率得到methyl 1-cyclopropyl-6-fluoro-4-oxo-7-(4-(11-(4-((quinolin-6-ylamino)methyl)-1H-1,2,3-triazol-1-yl)undecanoyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of Bioactive Complex Small Molecule–Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity

  摘要：

  Conjugates between pharmaceuticals and small molecules enable access to a vast chemical space required for the discovery of new lead molecules with modified therapeutic potential. However, the dearth of specific chemical reactions that are capable of functionalizing drugs and bioactive natural products presents a formidable challenge for preparing their conjugates. Here, we report a support-free CuI-nanoparticle-catalyzed strategy for conjugating electron-deficient and electron-rich terminal alkynes with a ciprofloxacin methyl ester. Our conjugation technique exploits the late-stage functionalization of bioactive natural products such as tocopherol, vasicinone, amino acids, and pharmaceuticals such as aspirin and paracetamol to provide conjugates in excellent yields under mild and green conditions. This protocol also enabled the synthesis of (hetero)arene-ciprofloxacin 1,4-disubstituted 1,2,3-triazoles in good yields and high regioselectivities. These synthesized ciprofloxacin conjugates were evaluated in vitro for their antibacterial activity against a panel of relevant bacteria. A significant number of conjugates showed comparable activity against Gram-positive and Gram-negative bacteria. Moreover, some conjugates exhibited less toxicity than ciprofloxacin against two mammalian cell lines, suggesting the utility for the future investigation of these compounds for in vivo efficacy and pharmacokinetic studies.

  DOI：

  10.1021/acscombsci.0c00060
• 作为产物：
  描述：

  N,N′-dipropargyl-p-phenylenediamine 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以34%的产率得到N-prop-2-yn-1-ylquinolin-6-amine
  参考文献：
  名称：

  N-炔丙基苯胺或炔丙基氨基香豆素在TiO 2上负载金纳米粒子催化合成喹啉和稠合吡啶并香豆素

  摘要：

  [5,6]-吡啶并香豆素是在温和的条件下通过负载在TiO 2上的金纳米粒子活化6-炔丙基氨基香豆素的三键而以极好的收率制备的。N-炔丙基苯胺与Au / TiO 2或Au / Al 2 O 3的类似反应导致喹啉的形成。

  DOI：

  10.1016/j.tet.2013.04.026

文献信息

• Synthesis of Bioactive Complex Small Molecule–Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity
  作者：Rahul Upadhyay、Rahul Kumar、Manoj Jangra、Rohit Rana、Onkar S. Nayal、Hemraj Nandanwar、Sushil K. Maurya

  DOI：10.1021/acscombsci.0c00060

  日期：2020.9.14

  Conjugates between pharmaceuticals and small molecules enable access to a vast chemical space required for the discovery of new lead molecules with modified therapeutic potential. However, the dearth of specific chemical reactions that are capable of functionalizing drugs and bioactive natural products presents a formidable challenge for preparing their conjugates. Here, we report a support-free CuI-nanoparticle-catalyzed strategy for conjugating electron-deficient and electron-rich terminal alkynes with a ciprofloxacin methyl ester. Our conjugation technique exploits the late-stage functionalization of bioactive natural products such as tocopherol, vasicinone, amino acids, and pharmaceuticals such as aspirin and paracetamol to provide conjugates in excellent yields under mild and green conditions. This protocol also enabled the synthesis of (hetero)arene-ciprofloxacin 1,4-disubstituted 1,2,3-triazoles in good yields and high regioselectivities. These synthesized ciprofloxacin conjugates were evaluated in vitro for their antibacterial activity against a panel of relevant bacteria. A significant number of conjugates showed comparable activity against Gram-positive and Gram-negative bacteria. Moreover, some conjugates exhibited less toxicity than ciprofloxacin against two mammalian cell lines, suggesting the utility for the future investigation of these compounds for in vivo efficacy and pharmacokinetic studies.
• Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
  作者：Theodoros S. Symeonidis、Ioannis N. Lykakis、Konstantinos E. Litinas

  DOI：10.1016/j.tet.2013.04.026

  日期：2013.6

  [5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.

  [5,6]-吡啶并香豆素是在温和的条件下通过负载在TiO 2上的金纳米粒子活化6-炔丙基氨基香豆素的三键而以极好的收率制备的。N-炔丙基苯胺与Au / TiO 2或Au / Al 2 O 3的类似反应导致喹啉的形成。