tert-butyl 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)piperazine-1-carboxylate | 1000285-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[4-[3-(5-nitrofuran-2-yl)-4,5-dihydro-1,2-oxazol-5-yl]phenyl]piperazine-1-carboxylate
• CAS: 1000285-23-3
• 化学式: C₂₂H₂₆N₄O₆
• 分子量: 442.472
• InChiKey: VPVYRYSJZWQOKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)piperazine-1-carboxylate 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 3-(5-nitrofuran-2-yl)-5-(4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)phenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Novel pyridyl nitrofuranyl isoxazolines show antibacterial activity against multiple drug resistant Staphylococcus species

  摘要：

  A novel series of pyridyl nitrofuranyl isoxazolines were synthesized and evaluated for their antibacterial activity against multiple drug resistant (MDR) Staphylococcus strains. Compounds with piperazine linker between the pyridyl group and isoxazoline ring showed better activity when compared to compounds without the piperazine linker. 3-Pyridyl nitrofuranyl isoxazoline with a piperazine linker was found to be more active than corresponding 2-and 4-pyridyl analogues with MICs in the range of 4-32 mu g/mL against MDR Staphylococcus strains. The eukaryotic toxicity of the compounds was tested by MTT assay and were found to be non-toxic against both non-tumour lung fibroblast WI-38 and cervical cancer cell line HeLa. The most active pyridyl nitrofuranyl isoxazoline compound showed improved activity against a panel of Staphylococcus strains compared to nitrofuran group containing antibiotic nitrofurantoin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.037
• 作为产物：
  描述：

  5-nitrofurfuraldoxime 在 盐酸 、 Oxone 、 三乙胺 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 tert-butyl 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Novel pyridyl nitrofuranyl isoxazolines show antibacterial activity against multiple drug resistant Staphylococcus species

  摘要：

  A novel series of pyridyl nitrofuranyl isoxazolines were synthesized and evaluated for their antibacterial activity against multiple drug resistant (MDR) Staphylococcus strains. Compounds with piperazine linker between the pyridyl group and isoxazoline ring showed better activity when compared to compounds without the piperazine linker. 3-Pyridyl nitrofuranyl isoxazoline with a piperazine linker was found to be more active than corresponding 2-and 4-pyridyl analogues with MICs in the range of 4-32 mu g/mL against MDR Staphylococcus strains. The eukaryotic toxicity of the compounds was tested by MTT assay and were found to be non-toxic against both non-tumour lung fibroblast WI-38 and cervical cancer cell line HeLa. The most active pyridyl nitrofuranyl isoxazoline compound showed improved activity against a panel of Staphylococcus strains compared to nitrofuran group containing antibiotic nitrofurantoin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.037

文献信息

• Discovery of novel isoxazolines as anti-tuberculosis agents
  作者：Rajendra P. Tangallapally、Dianqing Sun、Rakesh、Nageshwar Budha、Robin E.B. Lee、Anne J.M. Lenaerts、Bernd Meibohm、Richard E. Lee

  DOI：10.1016/j.bmcl.2007.09.048

  日期：2007.12

  Nitrofuranyl isoxazolines with increased proteolytic stability over nitrofuranyl amides were designed and synthesized leading to discovery of several compounds with potent in vitro anti-tuberculosis activity. However, their in vivo activity was limited by high protein binding and poor distribution. Consequently, a series of non-nitrofuran containing isoxazolines were prepared to determine if the core had residual anti-tuberculosis activity. This led to the discovery of novel isoxazoline 12 as anti-tuberculosis agent with a MIC90 value of 1.56 mu g/mL. (c) 2007 Elsevier Ltd. All rights reserved.
• Novel pyridyl nitrofuranyl isoxazolines show antibacterial activity against multiple drug resistant Staphylococcus species
  作者：Pietro Picconi、Priya Prabaharan、Jennifer L. Auer、Stephanie Sandiford、Francesco Cascio、Madiha Chowdhury、Charlotte Hind、Matthew E. Wand、J. Mark Sutton、Khondaker M. Rahman

  DOI：10.1016/j.bmc.2017.05.037

  日期：2017.8

  A novel series of pyridyl nitrofuranyl isoxazolines were synthesized and evaluated for their antibacterial activity against multiple drug resistant (MDR) Staphylococcus strains. Compounds with piperazine linker between the pyridyl group and isoxazoline ring showed better activity when compared to compounds without the piperazine linker. 3-Pyridyl nitrofuranyl isoxazoline with a piperazine linker was found to be more active than corresponding 2-and 4-pyridyl analogues with MICs in the range of 4-32 mu g/mL against MDR Staphylococcus strains. The eukaryotic toxicity of the compounds was tested by MTT assay and were found to be non-toxic against both non-tumour lung fibroblast WI-38 and cervical cancer cell line HeLa. The most active pyridyl nitrofuranyl isoxazoline compound showed improved activity against a panel of Staphylococcus strains compared to nitrofuran group containing antibiotic nitrofurantoin. (C) 2017 Elsevier Ltd. All rights reserved.