3-叠氮基-5-甲氧羰基-1,2,4-三唑 | 53566-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-叠氮基-5-甲氧羰基-1,2,4-三唑
• 英文名称: methyl 5-azido-1,2,4-triazole-3-carboxylate
• 英文别名: methyl 3-azido-1H-1,2,4-triazole-5-carboxylate；methyl 5-azido-1H-1,2,4-triazole-3-carboxylate
• CAS: 53566-46-4
• 化学式: C₄H₄N₆O₂
• 分子量: 168.115
• InChiKey: MSHJMHKWBFZBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氯苯乙炔 、 3-叠氮基-5-甲氧羰基-1,2,4-三唑 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 1.5h， 以92%的产率得到
  参考文献：
  名称：

  An ionic liquid promoted approach to bitriazolyl compounds as succinate–ubiquinone oxidoreductase inhibitors

  摘要：

  比特三唑基化合物是一种新型骨架，与现有的商业化 SQR 抑制杀菌剂完全不同，可为进一步开发 SQR 抑制剂提供新的线索。

  DOI：

  10.1039/c6nj02454h
• 作为产物：
  描述：

  5-氨基-1H-1,2,4-三氮唑-3-羧酸甲酯 在 硫酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 3.33h， 以53.1%的产率得到3-叠氮基-5-甲氧羰基-1,2,4-三唑
  参考文献：
  名称：

  Synthesis of Bitriazolyl Compounds via Huisgen Reaction

  摘要：

  DOI：

  10.3987/com-04-10202

文献信息

• PHOTOLABELING PROBES OF RIBAVIRIN AND EICAR
  作者：Qiongyou Wu、Fanqi Qu、Jinqiao Wan、Yi Xia、Ling Peng

  DOI：10.1081/ncn-200060336

  日期：2005.4.1

  order to study the mechanisms responsible for their antiviral effects using a photolabeling approach, we have developed photolabeling probes of ribavirin and EICAR, in which an azido group was introduced into the pseudobases of triazole and imidazole, respectively. The ribavirin photoprobes were obtained by directly coupling the azidotriazole to the protected ribose sugar, while the EICAR probe was prepared

  利巴韦林是迄今为止唯一可用于治疗丙型肝炎病毒感染的小分子，最近在紧急情况下用于治疗疾病早期的严重急性呼吸系统综合症患者。EICAR 是利巴韦林最有效的同系物之一，其抗病毒效力是利巴韦林的 10 到 100 倍。利巴韦林和 EICAR 抗病毒作用的潜在机制尚未明确阐明，但它们似乎相似。为了使用光标记方法研究其抗病毒作用的机制，我们开发了利巴韦林和 EICAR 的光标记探针，其中将叠氮基分别引入三唑和咪唑的假碱基中。利巴韦林光探针是通过将叠氮三唑直接偶联到受保护的核糖上而获得的，而 EICAR 探针是通过重氮化 AICAR 并随后用 NaN3 取代来制备的。所有这些探针都显示出快速、清晰的光化学反应，这表明它们是用于光标记研究的有前途的工具。
• Design, Synthesis, and Characterization of Photolabeling Probes for the Study of the Mechanisms of the Antiviral Effects of Ribavirin
  作者：Qiongyou Wu、Fanqi Qu、Jinqiao Wan、Xun Zhu、Yi Xia、Ling Peng

  DOI：10.1002/hlca.200490079

  日期：2004.4

  Ribavirin, the only small molecule available so far for treating hepatitis-C-virus infection, was recently used in an emergency context to treat patients with severe acute respiratory syndrome (SARS) in the early stages of the disease. To study the mechanisms responsible for the antiviral effects of ribavirin by using a photolabeling approach, we designed, synthesized, and characterized the azidotriazole

  利巴韦林是迄今为止唯一可用于治疗丙型肝炎病毒感染的小分子，最近在紧急情况下用于治疗疾病早期的重症急性呼吸综合征（SARS）患者。为了研究通过使用光标记方法引起病毒唑抗病毒作用的机制，我们设计，合成并表征了叠氮三唑核苷1和2作为病毒唑的光标记探针。这些探针通过执行与NaN的相应的溴代三唑核苷的亲核取代中合成3（方案2），或通过与受保护的核糖的azidotriazole直接连结（方案4）。叠氮三唑核苷1和2显示出快速，清晰的光化学反应，这表明它们是用于光标记研究的有希望的候选者。
• Bitriazolyl acyclonucleosides with antiviral activity against tobacco mosaic virus
  作者：Wei Li、Yi Xia、Zhijin Fan、Fanqi Qu、Qiongyou Wu、Ling Peng

  DOI：10.1016/j.tetlet.2008.02.139

  日期：2008.4

  Bitriazolyl acyclonucleosides were synthesized via the Huisgen reaction and then subjected to ammonolysis. The antiviral activity of these nucleosides against tobacco mosaic virus (TMV) was assessed. Like the previously described bitriazolyl compounds, these new bitriazolyl acyclonucleosides were found to show anti-TMV activity. This suggests that the bitriazolyl moieties are important structural features involved in the antiviral activity of these compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• Discovery of bitriazolyl compounds as novel antiviral candidates for combating the tobacco mosaic virus
  作者：Yi Xia、Zhijin Fan、Jianhua Yao、Quan Liao、Wei Li、Fanqi Qu、Ling Peng

  DOI：10.1016/j.bmcl.2006.02.023

  日期：2006.5

  Bitriazolyl compounds were synthesized and their activity against tobacco mosaic virus was assessed. Two of them showed promising antiviral activity and were more potent than the reference compounds. Moreover, these compounds are predicted not to be carcinogenic or mutagenic based on the prediction systems. Therefore, the bitriazolyl compounds may provide interesting new leads or scaffolds for use in further attempts to screen novel antiviral candidates. (C) 2006 Elsevier Ltd. All rights reserved.