N-(4-methoxyphenyl) 2,4-dinitrophenylsulfonamide

• 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: N-(4-methoxyphenyl) 2,4-dinitrophenylsulfonamide
• 英文别名: N-(4-methoxyphenyl)-2.4-dinitrobenzenesulfonamide；N-(4-methoxyphenyl)-2,4-dinitro-benzenesulfonamide；N-(4-methoxyphenyl)-2,4-dinitrobenzenesulfonamide
• 化学式: C₁₃H₁₁N₃O₇S
• 分子量: 353.312
• InChiKey: HGTSEBGNDLMIKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl) 2,4-dinitrophenylsulfonamide 在 L-半胱氨酸 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 生成 二氧化硫
  参考文献：
  名称：

  THIOL MEDIATED/ACTIVATED PRODRUGS OF SULFUR DIOXIDE (SO2) HAVING ANTI-BACTERIAL ACTIVITY

  摘要：

  本文披露了硫醇介导/激活的SO2前药，尤其是2,4-二硝基苯磺酰胺类似物，具有公式I或其药学上可接受的盐，表现出可调节的SO2释放剖面，并对细菌感染具有显著的治疗功效。此外，本发明提供了包含公式I化合物或其药学上可接受的盐的制药组合物，以及药学上可接受的载体/赋形剂。

  公开号：

  US20140121211A1
• 作为产物：
  描述：

  2,4-二硝基苯磺酰氯 、 甲氧苯胺 以 二氯甲烷 为溶剂， 以66%的产率得到N-(4-methoxyphenyl) 2,4-dinitrophenylsulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO₂) as Antimycobacterial Agents

  摘要：

  Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step from commercial sources, had a potency (MIC = 0.15 mu M) of inhibiting Mycobacterium tuberculosis (Mtb) higher than the clinical agent isoniazid (MIC = 0.37 mu M).

  DOI：

  10.1021/jm201023g

文献信息

• Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
  作者：Kundansingh A. Pardeshi、Satish R. Malwal、Ankita Banerjee、Surobhi Lahiri、Radha Rangarajan、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2015.04.046

  日期：2015.7

  are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in

  耐药感染在世界范围内变得越来越普遍，并且新的药物开发策略是必需的。在这里，我们报告2，4-二硝基苯磺酰胺的合成和评估，这是一种活性硫物质二氧化硫（SO 2）的供体，作为耐甲氧西林的金黄色葡萄球菌（MRSA）抑制剂。N-（3-甲氧基苯基）-2,4-二硝基-N-（prop-2-yn-1-yl）苯磺酰胺（5e）具有优异的体外MRSA抑制能力。该化合物具有细胞渗透性，并用5e耗尽的细胞内硫醇和增强的氧化物种处理MRSA细胞，两者的结果均与涉及硫醇活化以产生SO 2的机理一致。
• Synthesis and antimycobacterial activity of prodrugs of sulfur dioxide (SO2)
  作者：Satish R. Malwal、Dharmarajan Sriram、Perumal Yogeeswari、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2012.04.048

  日期：2012.6

  Here, we synthesized and studied a library of 2,4-dinitrophenylsulfonamides that closely resembled N-benzyl-2,4-dinitrophenylsulfonamide (1), a thiol-activated prodrug of sulfur dioxide (SO2) which has shown high potency as a Mycobacterium tuberculosis (Mtb) inhibitory agent. The ability of these compounds to generate SO2 in the presence of a thiol was evaluated. A good correlation between pK(aH) of the corresponding amine and reactivity with thiols to generate SO2 was found suggesting that the rate determining step of SO2 generation involved protonation of the amine. Amongst analogues with measurable MICs, we also found a correlation between ability to generate SO2 and Mtb growth inhibitory activity. Together, we report several thiol-mediated prodrugs of SO2 which strongly inhibited Mtb growth (MIC < 1 mu g mL(-1)) with potential for further development as tuberculosis drug candidates. (C) 2012 Elsevier Ltd. All rights reserved.
• Solid-phase synthesis of tertiary-amino linked benzamides: a versatile method for forming C–N bonds with electron-rich and electron-poor anilines
  作者：Kevin W. Gillman、Danielle Bocchino、Jeffrey W. Noonan、Milind Deshpande、Weixu Zhai

  DOI：10.1016/j.tetlet.2007.07.192

  日期：2007.10

  There currently are a wide variety of methods for forming C-N bonds on solid support. Two preferred methods are reductive aminations with resin bound amines or aldehydes as well as standard alkylation strategies. We herein disclose the scope and application of the Mitsunobu reaction of 2,4-dinitro-N-phenylbenzenesulfonamides derived from both electron-rich and electron-poor anilines as a practical and versatile addition to the repertoire of solid phase C-N bond forming reactions. (C) 2007 Elsevier Ltd. All rights reserved.
• US9079870B2
  申请人：——

  公开号：US9079870B2

  公开（公告）日：2015-07-14