N-benzyl-N-(1-propyl)-2,4-dinitrobenzenesulfonamide | 1352615-99-6

• 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-benzyl-N-(1-propyl)-2,4-dinitrobenzenesulfonamide
• 英文别名: (N-benzyl,N-propyl) 2,4-dinitrophenylsulfonamide；N-benzyl-2,4-dinitro-N-propyl-benzenesulfonamide；N-benzyl-2,4-dinitro-N-propylbenzenesulfonamide
• CAS: 1352615-99-6
• 化学式: C₁₆H₁₇N₃O₆S
• 分子量: 379.393
• InChiKey: XWRIOYOITNYPCE-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  549.9±60.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-(1-propyl)-2,4-dinitrobenzenesulfonamide 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 、 N-丙基苄胺 以 二氯甲烷 为溶剂， 以73%的产率得到N-benzyl-N-(1-propyl)-2,4-dinitrobenzenesulfonamide
  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

• 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.
• Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO₂) as Antimycobacterial Agents
  作者：Satish R. Malwal、Dharmarajan Sriram、Perumal Yogeeswari、V. Badireenath Konkimalla、Harinath Chakrapani

  DOI：10.1021/jm201023g

  日期：2012.1.12

  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).
• THIOL MEDIATED/ACTIVATED PRODRUGS OF SULFUR DIOXIDE (SO2) HAVING ANTI-BACTERIAL ACTIVITY
  申请人：INDIAN INSTITUTE OF SCIENCE EDUCATION AN

  公开号：US20140121211A1

  公开（公告）日：2014-05-01

  Disclosed herein are thiol mediated/activated prodrugs of SO 2 , particularly 2,4-dinitrophenylsulfonamide analogues, having Formula-I or pharmaceutically acceptable salts thereof exhibiting tunable release profiles of SO 2 with significant therapeutic efficacy against bacterial infections. Further, the present invention provides pharmaceutical compositions comprising compound of Formula I or pharmaceutically acceptable salts thereof, along with pharmaceutically acceptable carriers/excipients.

  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。