Ethyl 2-[4-[(3-ethynylphenyl)carbamoyl]triazol-1-yl]acetate | 1267623-22-2

• 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: Ethyl 2-[4-[(3-ethynylphenyl)carbamoyl]triazol-1-yl]acetate
• 英文别名: ethyl 2-[4-[(3-ethynylphenyl)carbamoyl]triazol-1-yl]acetate
• CAS: 1267623-22-2
• 化学式: C₁₅H₁₄N₄O₃
• 分子量: 298.301
• InChiKey: DRLIJRZAQKQGGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[4-[(3-ethynylphenyl)carbamoyl]triazol-1-yl]acetate 、 苄基叠氮 在 Amberlyst A-21 supported CuI 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到ethyl 2-(4-{[3-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl]carbamoyl}-1H-1,2,3-triazol-1-yl) acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes

  摘要：

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.025
• 作为产物：
  描述：

  3-氨基苯乙炔 在 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 Ethyl 2-[4-[(3-ethynylphenyl)carbamoyl]triazol-1-yl]acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes

  摘要：

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.025

文献信息

• Chemoselective preparation of disymmetric bistriazoles from bisalkynes
  作者：Hichem Elamari、Faouzi Meganem、Jean Herscovici、Christian Girard

  DOI：10.1016/j.tetlet.2010.11.141

  日期：2011.2

  Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen's reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes
  作者：Hichem Elamari、Riadh Slimi、Guy G. Chabot、Lionel Quentin、Daniel Scherman、Christian Girard

  DOI：10.1016/j.ejmech.2012.12.025

  日期：2013.2

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.