4-(4-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-1H-1,2,3-triazole | 1135334-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-1H-1,2,3-triazole
• 英文别名: 4-(4-Methoxyphenyl)-1-[(3-methoxyphenyl)methyl]triazole
• CAS: 1135334-77-8
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: VAZNVCICBGRZOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-1H-1,2,3-triazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到1-(3-hydroxybenzyl)-4-(4-hydroxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles

  摘要：

  In order to discover novel probes that may help in the investigation and the control of bacterial biofilms, we have designed a library of triazole-based analogs of 2-aminoimidazole marine alkaloids: naamine A and isonaamine A. Twenty-two compounds were screened for their biofilm inhibitory activity against two strains of Gram-negative bacteria. Four compounds were shown to act as non-toxic inhibitors of biofilm development without effect on bacterial growth even at high concentrations (100 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.050
• 作为产物：
  描述：

  3-甲氧基氯苄 在 sodium azide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 4-(4-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-1H-1,2,3-triazole
  参考文献：
  名称：

  芳基三唑衍生物及其羟基次甲基同系物对B16黑色素瘤细胞系的合成及细胞毒性评估。

  摘要：

  在这份手稿中，我们描述了一些三唑衍生物对B16黑色素瘤细胞系的合成和细胞毒性评估。为此，我们使用Besthmann-Ohira试剂将一组芳香醛转化为末端炔烃，并通过乙炔格氏试剂制备了相应的羟甲基同化炔烃。然后使用固体负载的催化剂（Amberlyst A-21 CuI）将这些生成的两组炔烃进行铜（I）催化的炔烃-叠氮化物环加成反应（CuAAC），第三组由有机叠氮化物组成。然后在体外针对B16黑色素瘤细胞系测试了合成的三唑。其中，化合物a1b1（R1 =对硝基苯基，R2 =苄基），a4b1（R1 =萘基，R2 =苄基）和a4b5（R1 =萘基，R2 =（R / S）-二氧戊环）表现出对B16的最佳活性黑色素瘤细胞

  DOI：

  10.1016/j.ejmech.2016.06.057

文献信息

• Azide–alkyne cycloaddition reactions in water <i>via</i> recyclable heterogeneous Cu catalysts: reverse phase silica gel and thermoresponsive hydrogels
  作者：Minkyung Lim、Heejin Lee、Minseok Kang、Woncheol Yoo、Hakjune Rhee

  DOI：10.1039/c8ra00306h

  日期：——

  Functionalized reverse phase silica gel and thermoresponsive hydrogels were synthesized as heterogeneous catalysts supports. Cu(I) and Cu(II) catalysts immobilized onto two types of supports were prepared and characterized. The copper catalyzed azide–alkyne cycloaddition was performed in water via a one-pot reaction and yielded good results. These catalysts are air stable and reusable over multiple

  合成了功能化的反相硅胶和热响应水凝胶作为非均相催化剂载体。制备并表征了固定在两种载体上的Cu( I ) 和 Cu( II ) 催化剂。铜催化的叠氮化物-炔烃环加成反应在水中通过一锅反应进行，并产生了良好的结果。这些催化剂对空气稳定且可多次使用。
• Azide–alkyne cycloadditions in a vortex fluidic device: enhanced “on water” effects and catalysis in flow
  作者：Gabriela Oksdath-Mansilla、Renata L. Kucera、Justin M. Chalker、Colin L. Raston

  DOI：10.1039/d0cc04401f

  日期：——

  Azide–alkyne cycloadditions in a Vortex Fluidic Device benefit from enhanced “on water” effects and copper jet feeds provide a convenient method of highly active catalyst delivery for flow chemistry.

  在旋涡流体装置中进行的叠氮-炔烃环加成反应受益于增强的“在水上”效应，铜喷嘴供给提供了一种便捷的高活性催化剂输送方法，适用于流动化学。
• Synthesis and cytotoxicity evaluation of aryl triazolic derivatives and their hydroxymethine homologues against B16 melanoma cell line
  作者：Shiva Kalhor-Monfared、Claire Beauvineau、Daniel Scherman、Christian Girard

  DOI：10.1016/j.ejmech.2016.06.057

  日期：2016.10

  third set composed of organic azides. Synthesized triazoles were then tested in vitro against B16 melanoma cell line. Amongst them, compounds a1b1 (R1 = p-nitrophenyl, R2 = benzyl), a4b1 (R1 = naphthyl, R2 = benzyl) and a4b5 (R1 = naphthyl, R2 = (R/S)- dioxolane) showed the best activity against B16 melanoma cells, with IC50 of 5.12, 3.89 and 6.60 muM respectively.

  在这份手稿中，我们描述了一些三唑衍生物对B16黑色素瘤细胞系的合成和细胞毒性评估。为此，我们使用Besthmann-Ohira试剂将一组芳香醛转化为末端炔烃，并通过乙炔格氏试剂制备了相应的羟甲基同化炔烃。然后使用固体负载的催化剂（Amberlyst A-21 CuI）将这些生成的两组炔烃进行铜（I）催化的炔烃-叠氮化物环加成反应（CuAAC），第三组由有机叠氮化物组成。然后在体外针对B16黑色素瘤细胞系测试了合成的三唑。其中，化合物a1b1（R1 =对硝基苯基，R2 =苄基），a4b1（R1 =萘基，R2 =苄基）和a4b5（R1 =萘基，R2 =（R / S）-二氧戊环）表现出对B16的最佳活性黑色素瘤细胞
• Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles
  作者：D. Linares、O. Bottzeck、O. Pereira、A. Praud-Tabariès、Y. Blache

  DOI：10.1016/j.bmcl.2011.09.050

  日期：2011.11

  In order to discover novel probes that may help in the investigation and the control of bacterial biofilms, we have designed a library of triazole-based analogs of 2-aminoimidazole marine alkaloids: naamine A and isonaamine A. Twenty-two compounds were screened for their biofilm inhibitory activity against two strains of Gram-negative bacteria. Four compounds were shown to act as non-toxic inhibitors of biofilm development without effect on bacterial growth even at high concentrations (100 mu M). (C) 2011 Elsevier Ltd. All rights reserved.