5-chloro-1-(4-nitrophenyl)-1H-benzo[d][1,2,3]triazole | 1256156-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-1-(4-nitrophenyl)-1H-benzo[d][1,2,3]triazole
• 英文别名: 5-chloro-1-(4-nitrophenyl)benzotriazole
• CAS: 1256156-79-2
• 化学式: C₁₂H₇ClN₄O₂
• 分子量: 274.666
• InChiKey: ARBIWKZJXPBIFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[(2,5-dichlorophenyl)diazenyl]-4-nitroaniline 在 copper(l) iodide 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 6.5h， 以84%的产率得到5-chloro-1-(4-nitrophenyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  A ligand-free copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes in PEG-water: an expeditious protocol towards regiospecific 1-aryl benzotriazoles

  摘要：

  通过铜 (1) 催化 2-Haloaryldiazonium 盐的重氮氨基苯在 PEG 水中的分子内 N-芳基化反应，我们开发出了一种高效且用途广泛的方法，用于合成作为重要药用支架的各种区域特异性 1-芳基苯并三唑。该方法的主要特点是反应方案非常简单、可负担大量底物以及收率极高。

  DOI：

  10.1039/c0ob00177e

文献信息

• Antiviral activities of 5-chlorobenzotriazole derivatives
  作者：Roberta Ibba、Paola Corona、Antonio Carta、Paolo Giunchedi、Roberta Loddo、Giuseppina Sanna、Ilenia Delogu、Sandra Piras

  DOI：10.1007/s00706-018-2234-7

  日期：2018.7

  In this study, we designed and synthesized a series of new 5-chlorobenzotriazole derivatives. Compounds were tested for cytotoxicity and antiviral activity in cell-based assays against several positive single-stranded RNA viruses: BVDV, YFV, CVB-5, and Sb-1; two negative single-stranded RNA viruses: RSV and VSV; a double-stranded RNA virus (Reo-1); and two DNA viruses: VV and HSV-1. N-[4-(5-Chloro-2H-benzo[d][1,2,3]triazol-2-yl)phenyl]-3,4,5-trimethoxybenzamide turned out to be the most potent compound against bovine viral diarrhea virus (BVDV). Its activity was shown to be comparable to the activity of the reference drug NM 107 (EC50 3.0 vs. 1.7 mu M). It is going to be used as a lead compound for future antiviral drug developments.[GRAPHICS].
• A ligand-free copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes in PEG-water: an expeditious protocol towards regiospecific 1-aryl benzotriazoles
  作者：Chhanda Mukhopadhyay、Pradip Kumar Tapaswi、Ray J. Butcher

  DOI：10.1039/c0ob00177e

  日期：——

  An efficient and highly versatile method for the synthesis of diverse regiospecific 1-arylbenzotriazoles being important medicinal scaffolds, by the copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes of 2-haloaryldiazonium salts in PEG-water has been developed. A very simple reaction protocol, large number of substrate affordability and excellent yields are the main features of this methodology.

  通过铜 (1) 催化 2-Haloaryldiazonium 盐的重氮氨基苯在 PEG 水中的分子内 N-芳基化反应，我们开发出了一种高效且用途广泛的方法，用于合成作为重要药用支架的各种区域特异性 1-芳基苯并三唑。该方法的主要特点是反应方案非常简单、可负担大量底物以及收率极高。