1-(4-aminophenyl)-1H-tetrazol-5(4H)-one | 99595-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-aminophenyl)-1H-tetrazol-5(4H)-one
• 英文别名: 1-(4-amino-phenyl)-1,4-dihydro-tetrazolone；1-(4-Amino-phenyl)-1,4-dihydro-tetrazolon；1-(4-aminophenyl)-4,5-dihydro-1H-1,2,3,4-tetrazol-5-one；4-(4-aminophenyl)-1H-tetrazol-5-one
• CAS: 99595-73-0
• 化学式: C₇H₇N₅O
• mdl: MFCD09808298
• 分子量: 177.165
• InChiKey: OKAOEKKGMDHTRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-aminophenyl)-1H-tetrazol-5(4H)-one 、 3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以10%的产率得到3,4-dichloro-5-methyl-N-(4-(5-oxo-4,5-dihydro-1H-tetrazol-1-yl)phenyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors

  摘要：

  ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1-50 mu M range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 mu M, 1.56 mu M, 0.78 mu M and 0.72 mu M, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 mu M on both strains, and MIC value of 32 mu M against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.004
• 作为产物：
  描述：

  1-(4-硝基苯基)-2H-四唑-5-酮 在 乙醇 、 铂 作用下， 生成 1-(4-aminophenyl)-1H-tetrazol-5(4H)-one
  参考文献：
  名称：

  The Synthesis of 1-Substituted 5(4H)Tetrazolinones^1a,b

  摘要：

  DOI：

  10.1021/ja01521a041

文献信息

• Substituent Effects on EI-MS Fragmentation Patterns of 5-Allyloxy-1-aryl-tetrazoles and 4-Allyl-1-aryl-tetrazole-5-ones; Correlation with UV-Induced Fragmentation Channels
  作者：Alina Secrieru、Rabah Oumeddour、Maria L. S. Cristiano

  DOI：10.3390/molecules26113282

  日期：——

  present work, we unravel the fragmentation patterns of a chemically diverse range of 5-allyloxy-1-aryl-tetrazoles and 4-allyl-1-aryl-tetrazolole-5-ones when subjected to electron impact mass spectrometry (EI-MS) and investigate the correlation with the UV-induced fragmentation channels of the matrix-isolated tetrazole derivatives. Our results indicate that the fragmentation pathways of the selected tetrazoles

  1,4-和1,5-二取代四唑具有丰富的结构和多功能的化学性质，对化学家来说是一个挑战。在目前的工作中，我们解开了化学多样化范围的 5-烯丙氧基-1-芳基-四唑和 4-烯丙基-1-芳基-四唑-5-酮在进行电子撞击质谱 (EI-MS) 时的裂解模式) 并研究与基质分离的四唑衍生物的紫外线诱导碎裂通道的相关性。我们的结果表明，EI-MS 中所选四唑的碎裂途径受取代诱导的电子效应的影响很大。可以设想多种途径来解释碎裂的机制，通常授予常见的最终物种，即芳基异氰酸酯、芳基叠氮化物、芳基硝基、异氰酸和叠氮化氢自由基阳离子，以及烯丙基/芳基阳离子。鉴定出的片段与先前研究中发现的有关同一类分子的光化学稳定性的片段一致。这种平行性展示了四唑在惰性气体低温基质惰性环境中 EI-MS 和紫外线照射下的行为的相似性，为反应性预测提供了有效的工具，无论是用于分析目的还是更深入的研究。理论计算提供了补充信息来阐明对结果
• The Synthesis of 1-Substituted 5(4H)Tetrazolinones^1a,b
  作者：Jerome P. Horwitz、Benjamin E. Fisher、Arthur J. Tomasewski

  DOI：10.1021/ja01521a041

  日期：1959.6
• An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors
  作者：Davide Benedetto Tiz、Žiga Skok、Martina Durcik、Tihomir Tomašič、Lucija Peterlin Mašič、Janez Ilaš、Anamarija Zega、Gábor Draskovits、Tamás Révész、Ákos Nyerges、Csaba Pál、Cristina D. Cruz、Päivi Tammela、Dušan Žigon、Danijel Kikelj、Nace Zidar

  DOI：10.1016/j.ejmech.2019.02.004

  日期：2019.4

  ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1-50 mu M range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 mu M, 1.56 mu M, 0.78 mu M and 0.72 mu M, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 mu M on both strains, and MIC value of 32 mu M against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action. (C) 2019 Elsevier Masson SAS. All rights reserved.