4-cyano-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene | 1083171-27-0

• 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-cyano-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene
• 英文别名: 4-[4-(3-Hydroxypropyl)triazol-1-yl]benzonitrile
• CAS: 1083171-27-0
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: ATPSXKBUYQHVRD-UHFFFAOYSA-N

物化性质

• 沸点：
  468.8±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-cyano-(4-(3-(tosyloxy)propyl)-1H-1,2,3-triazol-1-yl)benzene
  参考文献：
  名称：

  Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

  摘要：

  Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteasome. We previously published a study exploring the aryl sulfonate ester of cjoc42 in an effort to enhance gankyrin binding and inhibit cancer cell proliferation. In order to further improve the gankyrin binding ability of the cjoc42 scaffold, an extensive SAR for the aryl-triazole moiety of cjoc42 was developed. Our cjoc42 derivatives exhibited enhanced gankyrin binding, as well as enhanced antiproliferative activity against Hep3B, HepG2, A549, and MDA-MB-231 cancer cell lines.

  DOI：

  10.1016/j.bmcl.2020.127372
• 作为产物：
  描述：

  对氨基苯腈 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 4-cyano-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene
  参考文献：
  名称：

  Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

  摘要：

  Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteasome. We previously published a study exploring the aryl sulfonate ester of cjoc42 in an effort to enhance gankyrin binding and inhibit cancer cell proliferation. In order to further improve the gankyrin binding ability of the cjoc42 scaffold, an extensive SAR for the aryl-triazole moiety of cjoc42 was developed. Our cjoc42 derivatives exhibited enhanced gankyrin binding, as well as enhanced antiproliferative activity against Hep3B, HepG2, A549, and MDA-MB-231 cancer cell lines.

  DOI：

  10.1016/j.bmcl.2020.127372

文献信息

• Microwave Enhancement of a ‘One-Pot’ Tandem Azidation-‘Click’ Cycloaddition of Anilines
  作者：John. Moses、Adam Moorhouse

  DOI：10.1055/s-2008-1078019

  日期：2008.8

  The practical and efficient one-pot azidation of anilines with the reagent combination t-BuONO and TMSN3 has become a useful addition to the click-chemistry toolbox. Herein we report a modification of this methodology, using microwave radiation to significantly enhance the rate of formation of 1,4-triazoles from in situ generated azides.

  一种实用高效的一锅式芳胺叠氮化反应，采用试剂组合t-BuONO和TMSN3，已成为“点击化学”工具箱中的有用补充。在此，我们报告了该方法的一个改进，使用微波辐射显著提高了由原位生成的叠氮化物形成1,4-三唑的速率。