2-Bromo-N-(2-chloro-4-sulfamoyl-phenyl)-propionamide | 53298-00-3

• 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-Bromo-N-(2-chloro-4-sulfamoyl-phenyl)-propionamide
• 英文别名: 2-bromo-N-(2-chloro-4-sulfamoylphenyl)propanamide
• CAS: 53298-00-3
• 化学式: C₉H₁₀BrClN₂O₃S
• 分子量: 341.613
• InChiKey: CLUZBEDAQBTAHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Bromo-N-(2-chloro-4-sulfamoyl-phenyl)-propionamide 、 2-chloro-9-(4-cyclopropylnaphthalen-1-yl)-9H-purine-8-thiol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以70.6%的产率得到N-(2-chloro-4-sulfamoylphenyl)-2-((2-chloro-9-(4-cyclopropylnaphthalen-1-yl)-9H-purin-8-yl)thio)propanamide
  参考文献：
  名称：

  Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach

  摘要：

  By means of structure-based bioisosterism approach, a series of novel purinylthioacetanilide derivatives were designed, synthesized and evaluated as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Some of the tested compounds were found to be active against wild-type (WT) HIV-1 (IIIB) with EC50 in the range of 0.78-4.46 mu M. Among them, LAD-8 displayed the most potent anti-HIV activity (EC50 = 0.78 mu M, SI = 24). In addition, LBD-6 showed moderate activity against L100I mutant (EC50 = 5.64 mu M) and double mutant strain RES056 (EC50 = 22.24 mu M). Preliminary structure-activity relationships (SARs) were discussed in detail. Molecular modeling study was used to predict the optimal conformation in the NNRTI binding site, which may play a guiding role in further rational optimization. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.07.041