3-acetyl-5-(4-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole | 1391119-83-7

• 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-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole
• 英文别名: 1-(2-(5-nitrofuran-2-yl)-5-phenyl-1,3,4-oxadiazol-3(2H)-yl)ethanone；1-[2-(5-nitro-2-furyl)-5-phenyl-2H-1,3,4-oxadiazol-3-yl]ethanone；1-[2-(5-nitrofuran-2-yl)-5-phenyl-2H-1,3,4-oxadiazol-3-yl]ethanone
• CAS: 1391119-83-7
• 化学式: C₁₄H₁₁N₃O₅
• 分子量: 301.258
• InChiKey: HGPKTFGSATYETK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  苯甲酰肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-acetyl-5-(4-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and testing of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives for antifungal activity against selected Candida Species

  摘要：

  A series of 21 1,3,4-oxadiazoline derivatives was synthesized by cyclization of N-acylhydrazones with acetic anhydride and evaluated for their in vitro antifungal activity against six Candida strains: Candida albicans (ATCC 90028 and LM V-42), C. krusei (ATCC 6258 and LM 12 C) and C. tropicalis (ATCC 13803 and LM 14). The Candida strains were found to be sensitive to some of the compounds, which inhibited the growth by 50-90%, with minimum inhibitory concentration (MIC) in the range of 64-512 mu g mL(-1). The compounds' structures were fully confirmed and characterized by Fourier transform infrared spectroscopy (FTIR), H-1 and C-13 nuclear magnetic resonance (NMR) and mass spectrometry (MS).

  DOI：

  10.1590/s0103-50532013000100016

文献信息

• Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives
  作者：Cledualdo Soares de Oliveira、Bruno Freitas Lira、Vivyanne dos Santos Falcão-Silva、Jose Pinto Siqueira-Junior、Jose Maria Barbosa-Filho、Petronio Filgueiras de Athayde-Filho

  DOI：10.3390/molecules17055095

  日期：——

  acetic anhydride under reflux conditions. Their structures were fully characterized by IR, ¹H-NMR, and ¹³C-NMR. Furthermore, evaluations of the antibacterial activity of the 1,3,4-oxadiazoles 5a-e and N-acylhydrazones 4a-e showed strong activity against several strains of Staphylococcus aureus, with MICs between 4 μg/mL to 32 μg/mL. In silico studies of the parameters of Lipinski's Rule of Five, as well

  通过N环化合成了五种新的1-(2-(5-硝基呋喃-2-基)-5-(芳基)-1,3,4-恶二唑-3-(2H)-基)乙酮化合物5a-e -酰腙4a-e与乙酸酐在回流条件下反应。它们的结构通过IR、1H-NMR和13C-NMR进行了充分表征。此外，1,3,4-恶二唑 5a-e 和 N-酰基腙 4a-e 的抗菌活性评估显示，对多种金黄色葡萄球菌菌株具有很强的活性，MIC 介于 4 μg/mL 至 32 μg/mL 之间。对 Lipinski 五法则参数以及拓扑极性表面积 (TPSA)、吸收百分比 (% ABS)、药物相似性和药物评分的计算机研究表明，这些化合物，特别是 4a 和 5d，有潜力成为新候选药物。
• 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.
• 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.