3-fluoro-benzonitrile N-oxide | 1093649-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-fluoro-benzonitrile N-oxide
• 英文别名: 3-fluorobenzonitrile N-oxide；3-fluorobenzonitrile oxide
• CAS: 1093649-55-8
• 化学式: C₇H₄FNO
• 分子量: 137.113
• InChiKey: PYKHEEPCZUMOAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-fluoro-benzonitrile N-oxide 在 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3-(3-fluorophenyl)-N-hydroxy-5-methyl-4,5-dihydroisoxazole-5-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease

  摘要：

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.

  DOI：

  10.1021/jm400902y
• 作为产物：
  描述：

  3-氟苯甲醛肟 在 N-氯代丁二酰亚胺 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 3-fluoro-benzonitrile N-oxide
  参考文献：
  名称：

  二苯并氮杂连接的异恶唑：新型有效的α-葡萄糖苷酶抑制剂

  摘要：

  α-葡萄糖苷酶抑制是控制糖尿病高血糖的有效方法。在目前的研究中，根据他们作为抗糖尿病药物的文献，设计了作为异恶唑和二苯并氮杂支架混合体的新分子。为此，使用氧化腈-炔环加成 (NOAC) 反应制备了一系列二苯并氮杂连接的异恶唑 ( 33-54 )，并评估了它们的α-葡萄糖苷酶抑制活性，以探索治疗糖尿病的新方法。大多数化合物显示出对强效的抑制效力α葡糖苷酶（EC 3.2.1.20）的酶（IC 50 = 35.62±1.48至333.30±1.67 μ M）使用阿卡波糖作为参考药物（IC 50= 875.75 ± 2.08 µ M)。还确定了活性异恶唑的构效关系、动力学和分子对接研究，以研究酶-抑制剂相互作用。化合物33，40，41，46，48-50，和54显示结合与关键的氨基酸残基相互作用α葡糖苷酶的酶，如Lys156，Ser157，Asp242和Gln353。

  DOI：

  10.1016/j.bmcl.2021.127979

文献信息

• Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
  作者：Leonardo Di Nunno、Paola Vitale、Antonio Scilimati

  DOI：10.1016/j.tet.2008.09.063

  日期：2008.12

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin
  作者：Jabeena Khazir、Parvinder Pal Singh、D. Mahendhar Reddy、Irfan Hyder、Syed Shafi、S.D. Sawant、Gousia Chashoo、Ajay Mahajan、M.S. Alam、A.K. Saxena、S. Arvinda、B.D. Gupta、H.M. Sampath Kumar

  DOI：10.1016/j.ejmech.2013.01.003

  日期：2013.5

  In the present study, novel Spiro derivatives of alpha-santonin were prepared and tested for their anticancer activity against a panel of six human cancer cell lines. Spiro-isoxazoline and spiro-isoxazolidine derivatives have been generated on C-ring of alpha-santonin (alpha-methylene-gamma-butyrolactone) by the 1,3-dipolar cycloaddition of alpha-santonin derivative 6 with nitrile oxides 7 and nitrones 9 respectively. Among all, compound 10b '' had shown IC50 of 0.01, 0.5 and 0.3 mu M against PC-3, THP-1 and MCF-7 cell lines respectively. Further, flow cytometry studies showed that PC-3 cells treated with the spiro-isoxazolidine derivative 10b '' were arrested in the sub G1 phase of the cell cycle in a concentration dependent manner. The spiro-isoxazolidine derivative 10b '' also showed concentration dependent inhibitory activity against NF-kappa B, p65 with 57% inhibition in 24 h at 10 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 3-Aryl-5-halomethylisoxazoles. A New Class of Anthelmintics
  作者：H. G. Sen、D. Seth、U. N. Joshi、P. Rajagopalan

  DOI：10.1021/jm00321a048

  日期：1966.5
• Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease
  作者：Giseli Capaci Rodrigues、Daniel Ferreira Feijó、Marcelo Torres Bozza、Peiwen Pan、Daniela Vullo、Seppo Parkkila、Claudiu T. Supuran、Clemente Capasso、Alcino Palermo Aguiar、Alane Beatriz Vermelho

  DOI：10.1021/jm400902y

  日期：2014.1.23

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.
• Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors
  作者：Umm-E-Farwa、Saeed Ullah、Maria Aqeel Khan、Humaira Zafar、Atia-tul-Wahab、Munisaa Younus、M. Iqbal Choudhary、Fatima Z. Basha

  DOI：10.1016/j.bmcl.2021.127979

  日期：2021.5

  diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33-54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes

  α-葡萄糖苷酶抑制是控制糖尿病高血糖的有效方法。在目前的研究中，根据他们作为抗糖尿病药物的文献，设计了作为异恶唑和二苯并氮杂支架混合体的新分子。为此，使用氧化腈-炔环加成 (NOAC) 反应制备了一系列二苯并氮杂连接的异恶唑 ( 33-54 )，并评估了它们的α-葡萄糖苷酶抑制活性，以探索治疗糖尿病的新方法。大多数化合物显示出对强效的抑制效力α葡糖苷酶（EC 3.2.1.20）的酶（IC 50 = 35.62±1.48至333.30±1.67 μ M）使用阿卡波糖作为参考药物（IC 50= 875.75 ± 2.08 µ M)。还确定了活性异恶唑的构效关系、动力学和分子对接研究，以研究酶-抑制剂相互作用。化合物33，40，41，46，48-50，和54显示结合与关键的氨基酸残基相互作用α葡糖苷酶的酶，如Lys156，Ser157，Asp242和Gln353。