2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(2,4-dichlorophenyl)ethanol | 163729-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(2,4-dichlorophenyl)ethanol
• 英文别名: 2-(Benzotriazol-1-yl)-1-(2,4-dichlorophenyl)ethanol
• CAS: 163729-38-2
• 化学式: C₁₄H₁₁Cl₂N₃O
• 分子量: 308.167
• InChiKey: CGWJOHXRJWEHLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(2,4-dichlorophenyl)ethanol 、 4-氯苄溴 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到1-(2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents

  摘要：

  Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 mu g/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.041
• 作为产物：
  描述：

  T406石油添加剂 、 Alpha-(氯甲基)-2,4-二氯苯甲醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以25%的产率得到2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(2,4-dichlorophenyl)ethanol
  参考文献：
  名称：

  Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents

  摘要：

  Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 mu g/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.041

文献信息

• Design and synthesis of 1H-1,2,3-triazoles derived from econazole as antitubercular agents
  作者：Suhyun Kim、Sang-Nae Cho、Taegwon Oh、Pilho Kim

  DOI：10.1016/j.bmcl.2012.09.041

  日期：2012.11

  Econazole has been known to be active against Mycobacterium tuberculosis. We have designed and synthesized 1H-1,2,3-triazoles derived from econazole as antitubercular agents. The majority of triazole derivatives have been prepared by microwave-assisted click chemistry. It turned out that all of the prepared triazoles had no antifungal activities. However, most of the hydroxy-triazoles (6a and 10) apparently turned out to have antitubercular activities. Overall, hydroxy-triazoles 10 were more active than their corresponding ether-triazoles 11. While the MIC value of hydroxy-triazole 10d was as good as econazole (16 mu g/mL), the MIC value of 10a was two-fold more active than econazole, suggesting that this 1H-1,2,3-triazole scaffold (3) could be further optimized to develop Mtb specific agents. (C) 2012 Elsevier Ltd. All rights reserved.