N-苄基,N-(2-苯基乙基)2,4-二硝基苯基磺酰胺 | 1380698-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基,N-(2-苯基乙基)2,4-二硝基苯基磺酰胺
• 英文名称: N-benzyl, N-(2-phenylethyl) 2,4-dinitrophenylsulfonamide
• 英文别名: N-benzyl-2,4-dinitro-N-phenethylbenzenesulfonamide；N-benzyl-2,4-dinitro-N-phenethyl-benzenesulfonamide；N-benzyl-2,4-dinitro-N-(2-phenylethyl)benzenesulfonamide
• CAS: 1380698-40-7
• 化学式: C₂₁H₁₉N₃O₆S
• 分子量: 441.464
• InChiKey: FTIOZBFLDOHMDW-UHFFFAOYSA-N

物化性质

• 沸点：
  632.1±65.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  L-半胱氨酸 、 N-苄基,N-(2-苯基乙基)2,4-二硝基苯基磺酰胺 以 乙腈 为溶剂， 生成 (S-2,4-dinitrophenyl)cysteine
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of prodrugs of sulfur dioxide (SO2)

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.04.048

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.