4-(5-oxo-1,4-dihydrotetrazol-1-yl)benzoic acid methyl ester | 1207759-86-1

• 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-(5-oxo-1,4-dihydrotetrazol-1-yl)benzoic acid methyl ester
• 英文别名: methyl 4-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)benzoate；Methyl 4-(5-oxo-4,5-dihydro-1h-tetrazol-1-yl) benzoate；methyl 4-(5-oxo-1H-tetrazol-4-yl)benzoate
• CAS: 1207759-86-1
• 化学式: C₉H₈N₄O₃
• 分子量: 220.188
• InChiKey: QJTVKRZCAQGOCA-UHFFFAOYSA-N

物化性质

• 熔点：
  219 °C (decomp)(Solv: ethyl acetate (141-78-6))
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-金刚烷醇 、 4-(5-oxo-1,4-dihydrotetrazol-1-yl)benzoic acid methyl ester 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 以81%的产率得到1-(4-methoxycarbonylphenyl)-3-(1-adamantyl)-1H-tetrazolium-5-olate
  参考文献：
  名称：

  Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

  摘要：

  Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantylazoles and thus have potential for developing antiviral agents with an alternate mechanism of action. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.047
• 作为产物：
  描述：

  甲醇 、 4-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)benzoic acid 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以70%的产率得到4-(5-oxo-1,4-dihydrotetrazol-1-yl)benzoic acid methyl ester
  参考文献：
  名称：

  Adamantylazoles: XII. Alkylation of 1-R-tetrazole-5-thiones and 1-R-tetrazol-5-ones with tertiary alcohols in sulfuric acid

  摘要：

  1-R-Substituted tetrazole-5-thiones reacted with adamantan-1-ol in sulfuric acid to give mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-thiolates, isomeric 1-R-5-(1-adamantylsulfanyl)tetrazoles, 1-R-4-(1-adamantyl) tetrazole-5-thiones, and 1-R-3-(1-adamantyl)-5-(1-adamantylsulfanyl)tetrazolium salts. Adamantylation of 1-R-tetrazol-5-ones under analogous conditions afforded only the corresponding mesoionic 1-R-3-(1-adamantyl)tetrazolium-5-olates. Mesoionic 1-R-3-tert-butyltetrazolium-5-thiolates and 1-R-3-tert-butyltetrazolium-5-olates were obtained by alkylation of the same substrates with tert-butyl alcohol in sulfuric acid.

  DOI：

  10.1134/s1070363209100235