2-(2-nitrophenoxy)-N-(4-sulfamoylphenyl)acetamide

• 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: 2-(2-nitrophenoxy)-N-(4-sulfamoylphenyl)acetamide
• 化学式: C₁₄H₁₃N₃O₆S
• 分子量: 351.34
• InChiKey: MVIOLLJLCJUMMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenoxy)-N-(4-sulfamoylphenyl)acetamide 在 铁粉 、 氯化铵 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors

  摘要：

  Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 mu mol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 mu mol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations. (C) 2014 Yong-Tang Zheng and Xiao-Dong Ma. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.11.004
• 作为产物：
  描述：

  2-硝基苯氧乙酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 2-(2-nitrophenoxy)-N-(4-sulfamoylphenyl)acetamide
  参考文献：
  名称：

  Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors

  摘要：

  Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 mu mol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 mu mol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations. (C) 2014 Yong-Tang Zheng and Xiao-Dong Ma. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.11.004

文献信息

• Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors
  作者：Yong Sun、Cui-Lin Lu、Chang-Yuan Wang、Rui-Rui Wang、Ke-Xin Liu、Liu-Meng Yang、Yu-Hong Zhen、Hou-Li Zhang、Chao Wang、Yong-Tang Zheng、Xiao-Dong Ma

  DOI：10.1016/j.cclet.2014.11.004

  日期：2015.2

  Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 mu mol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 mu mol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations. (C) 2014 Yong-Tang Zheng and Xiao-Dong Ma. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.