3-acetyl-5-(4-n-butyl-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole | 1449763-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-acetyl-5-(4-n-butyl-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole
• 英文别名: 3-acetyl-5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole；1-[5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2H-1,3,4-oxadiazol-3-yl]ethanone
• CAS: 1449763-69-2
• 化学式: C₁₈H₁₉N₃O₅
• 分子量: 357.366
• InChiKey: IPZSNWYYYAJHGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-丁基苯甲酸 在 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 17.5h， 生成 3-acetyl-5-(4-n-butyl-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: Design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis

  摘要：

  The anti-Trypanosoma cruzi activity of 5-nitro-2-furfuriliden derivatives as well as the cytotoxicity of these compounds on J774 macrophages cell line and FN1 human fibroblast cells were investigated in this study. The most active compounds of series I and II were 4-butyl-[N'-(5-nitrofuran-2-y1) methylene] benzidrazide (3g; IC50= 1.05 mu M +/- 0.07) and 3-acety1-5-(4-butylpheny1)-2-(5-nitrofuran-2-y1)-2,3-dihydro,1,3,4-oxadiazole (4g; IC50 = 8.27 mu M +/- 0.42), respectively. Also, compound 3g was more active than the standard drugs, benznidazole (IC50= 22.69 u mu M 1.96) and nifurtimox (IC50= 3.78 mu M +/- 0.10). Regarding the cytotoxicity assay, the 3g compound presented IC50 value of 28.05 mu M (SI = 26.71) against J774 cells. For the FN1 fibroblast assay, 3g showed IC50 value of 98 mu M (SI = 93.33). On the other hand, compound 4g presented a cytotoxicity value on J774 cells higher than 400 mu M (SI >48), and for the FN1 cells its IC50 value was 186 mu M (SI = 22.49). Moreover, an exploratory data analysis, which comprises hierarchical cluster (HCA) and principal component analysis (PCA), was carried out and the findings were complementary. The molecular properties that most influenced the compounds' grouping were ClogP and total dipole moment, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel potential anti-T. cruzi molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.017

文献信息

• Exploring 5-nitrofuran derivatives against nosocomial pathogens: Synthesis, antimicrobial activity and chemometric analysis
  作者：Rodrigo Rocha Zorzi、Salomão Dória Jorge、Fanny Palace-Berl、Kerly Fernanda Mesquita Pasqualoto、Leandro de Sá Bortolozzo、André Murillo de Castro Siqueira、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2014.03.044

  日期：2014.5

  The burden of nosocomial or health care-associated infection (HCAI) is increasing worldwide. According to the World Health Organization (WHO), it is several fold higher in low-and middle-income countries. Considering the multidrug-resistant infections, the development of new and more effective drugs is crucial. Herein, two series (I and II) of 5-nitrofuran derivatives were designed, synthesized and assayed against microorganisms, including Gram-positive and -negative bacteria, and fungi. The pathogens screened was directly related to either the most currently relevant HCAI, or to multidrug-resistant infection caused by MRSA/VRSA strains, for instance. The sets I and II were composed by substituted[ N'-(5-nitrofuran-2-yl)methylene]benzhydrazide and 3-acetyl-5-(substituted-phenyl)-2-(5-nitro-furan-2-yl)-2,3-dihydro-1,3,4-oxadiazole compounds, respectively. The selection of the substituent groups was based upon physicochemical properties, such as hydrophobicity and electronic effect. The compounds have showed better activity against Staphylococcus aureus, Escherichia coli, and Enterococcus faecalis. The findings from S. aureus strain, which was more susceptible, were used to investigate the intersamples and intervariables relationships by applying chemometric methods. It is noteworthy that the compound 4-butyl-[N'-(5-nitrofuran-2-yl) methylene] benzhydrazide has showed similar MIC value to vancomycin, which is the reference drug for multidrug-resistant S. aureus infections. Taken the findings together, the 5-nitrofuran derivatives might be indeed considered as promising hits to develop novel antimicrobial drugs to fight against nosocomial infection. (C) 2014 Elsevier Ltd. All rights reserved.
• 5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: Design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis
  作者：Fanny Palace-Berl、Salomão Dória Jorge、Kerly Fernanda Mesquita Pasqualoto、Adilson Kleber Ferreira、Durvanei Augusto Maria、Rodrigo Rocha Zorzi、Leandro de Sá Bortolozzo、José Ângelo Lauletta Lindoso、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2013.06.017

  日期：2013.9

  The anti-Trypanosoma cruzi activity of 5-nitro-2-furfuriliden derivatives as well as the cytotoxicity of these compounds on J774 macrophages cell line and FN1 human fibroblast cells were investigated in this study. The most active compounds of series I and II were 4-butyl-[N'-(5-nitrofuran-2-y1) methylene] benzidrazide (3g; IC50= 1.05 mu M +/- 0.07) and 3-acety1-5-(4-butylpheny1)-2-(5-nitrofuran-2-y1)-2,3-dihydro,1,3,4-oxadiazole (4g; IC50 = 8.27 mu M +/- 0.42), respectively. Also, compound 3g was more active than the standard drugs, benznidazole (IC50= 22.69 u mu M 1.96) and nifurtimox (IC50= 3.78 mu M +/- 0.10). Regarding the cytotoxicity assay, the 3g compound presented IC50 value of 28.05 mu M (SI = 26.71) against J774 cells. For the FN1 fibroblast assay, 3g showed IC50 value of 98 mu M (SI = 93.33). On the other hand, compound 4g presented a cytotoxicity value on J774 cells higher than 400 mu M (SI >48), and for the FN1 cells its IC50 value was 186 mu M (SI = 22.49). Moreover, an exploratory data analysis, which comprises hierarchical cluster (HCA) and principal component analysis (PCA), was carried out and the findings were complementary. The molecular properties that most influenced the compounds' grouping were ClogP and total dipole moment, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel potential anti-T. cruzi molecules. (C) 2013 Elsevier Ltd. All rights reserved.