(R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)quinoline-8-sulfonamide | 1430414-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)quinoline-8-sulfonamide
• 英文别名: N-[[(5R)-3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]quinoline-8-sulfonamide；N-[[(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]quinoline-8-sulfonamide
• CAS: 1430414-11-1
• 化学式: C₂₃H₂₃FN₄O₅S
• 分子量: 486.524
• InChiKey: IGYYSWWEABQOGM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  吗啉恶酮相关物质A 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)quinoline-8-sulfonamide
  参考文献：
  名称：

  Synthesis, biological evaluation of new oxazolidino-sulfonamides as potential antimicrobial agents

  摘要：

  A number of linezolid-like oxazolidino-sulfonamides (7a-y and 8a-b) were designed and synthesized with a view to develop antimicrobial agents with improved properties. Most of the synthesized compounds showed good to moderate activity against a panel of standard Gram-positive and Gram-negative bacteria and fungal strains. The compounds 7i and 7v exhibited significant activity, with a MIC value of 2.0-6.0 mu g/mL against a panel of Gram-positive and Gram-negative bacteria. These compounds also showed activity against Candida albicans, with a MIC value of 4.0 mu g/mL. A correlation of the antimicrobial activity with calculated lipophilicity values (C log P) is also presented. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.034

文献信息

• 噁唑烷酮类化合物在制备抗冠状病毒药物中的应用
  申请人：宁波大学科学技术学院

  公开号：CN114129570B

  公开（公告）日：2023-04-25

  本发明公开了一种噁唑烷酮类化合物在制备抗冠状病毒药物中的应用，该抗冠状病毒药物含有噁唑烷酮类化合物作为活性成分，所述的噁唑烷酮类化合物为冠状病毒3CL蛋白酶抑制剂。本发明利用荧光探针法对通式I的噁唑烷酮类化合物进行酶活性测试，证明其对冠状病毒3CL蛋白酶具有抑制活性，可作为一种潜在的治疗和预防SARS病毒感染的药物。
• Synthesis and SARS-CoV-2 3CL Protease Inhibitory Effects of Oxazolidinone Derivatives
  作者：Shengxian Zhao、Chaojie Wang、Yiming Lu、Xin Zhang、Siyu Wu、Hui Mao

  DOI：10.21577/0103-5053.20220033

  日期：——

  The 3-chymotrypsin-like protease (3CLpro) is an attractive target for the development of anti- SARS (severe acute respiratory syndrome) drugs. In this work, a series of oxazolidinone derivatives 3a-3v were synthesized and their inhibitory activities against SARS coronavirus 2 (SARS-CoV-2) 3CLpro were evaluated by the fluorescence resonance energy transfer (FRET)-based enzymatic assay. Among synthesized compounds, 3g displayed the best inhibitory activity, with a half maximal inhibitory concentration (IC50) value of 14.47 μM. Also, docking studies implied that compound 3g was fitted into the active pocket of 3CLpro, forming a hydrogen bond with Glu166.

  3-糜蛋白酶样蛋白酶（3CLpro）是开发抗 SARS（严重急性呼吸系统综合征）药物的一个有吸引力的靶点。本研究合成了一系列噁唑烷酮衍生物 3a-3v，并通过基于荧光共振能量转移（FRET）的酶联测定评估了它们对 SARS 冠状病毒 2（SARS-CoV-2）3CLpro 的抑制活性。在合成的化合物中，3g 的抑制活性最好，其半最大抑制浓度（IC50）为 14.47 μM。同时，对接研究表明，化合物 3g 与 3CLpro 的活性口袋相吻合，并与 Glu166 形成氢键。
• Synthesis, biological evaluation of new oxazolidino-sulfonamides as potential antimicrobial agents
  作者：Ahmed Kamal、P. Swapna、Rajesh V.C.R.N.C. Shetti、Anver Basha Shaik、M.P. Narasimha Rao、Soma Gupta

  DOI：10.1016/j.ejmech.2013.01.034

  日期：2013.4

  A number of linezolid-like oxazolidino-sulfonamides (7a-y and 8a-b) were designed and synthesized with a view to develop antimicrobial agents with improved properties. Most of the synthesized compounds showed good to moderate activity against a panel of standard Gram-positive and Gram-negative bacteria and fungal strains. The compounds 7i and 7v exhibited significant activity, with a MIC value of 2.0-6.0 mu g/mL against a panel of Gram-positive and Gram-negative bacteria. These compounds also showed activity against Candida albicans, with a MIC value of 4.0 mu g/mL. A correlation of the antimicrobial activity with calculated lipophilicity values (C log P) is also presented. (C) 2013 Elsevier Masson SAS. All rights reserved.