N-[5-chloro-2-[2-(2-methyl-4-sulfamoyl-anilino)-2-oxo-ethoxy]phenyl]-3,4-dimethyl-benzamide | 1416363-96-6

• 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-[5-chloro-2-[2-(2-methyl-4-sulfamoyl-anilino)-2-oxo-ethoxy]phenyl]-3,4-dimethyl-benzamide
• 英文别名: N-[5-chloro-2-[2-(2-methyl-4-sulfamoylanilino)-2-oxoethoxy]phenyl]-3,4-dimethylbenzamide
• CAS: 1416363-96-6
• 化学式: C₂₄H₂₄ClN₃O₅S
• 分子量: 501.991
• InChiKey: GCZMATZWHYCJTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯-2-硝基苯酚 在 氯化亚砜 、 四丁基溴化铵 、 铁粉 、 碳酸氢钠 、 potassium carbonate 、 氯化铵 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 18.67h， 生成 N-[5-chloro-2-[2-(2-methyl-4-sulfamoyl-anilino)-2-oxo-ethoxy]phenyl]-3,4-dimethyl-benzamide
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and docking studies of N-phenylarylformamide derivatives (PAFAs) as non-nucleoside HIV reverse transcriptase inhibitors

  摘要：

  A series of N-phenylarylformamide derivatives (PAFAs) with anti-wild-type HIV-1 activity (EC50 values) ranging from 0.3 nM to 5.1 nM and therapeutic index (TI) ranging from 10 616 to 271 000 were identified as novel non-nucleoside reverse transcriptase inhibitors. Among them, compound 13g (EC50 = 0.30 nM, TI = 184 578), 131 (EC50 = 0.37 nM, TI = 212 819), 13m (EC50 = 0.32 nM, TI = 260 617) and 13r (EC50 = 0.27 nM, TI = 271 000) displayed the highest activity against this type virus nearly as potent as lead compound GW678248. Moreover, all of them were also active to inhibit the double mutant strain A(17) (K103N + Y181C) with EC50 values of 0.29 mu M, 0.14 mu M, 0.10 mu M and 0.27 mu M, respectively. In particular, compound 13m, which showed broad-spectrum anti-HIV activity, was also effective to inhibit the HIV-2 ROD replication within 4.37 mu M concentration. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.032

文献信息

• Synthesis, structure–activity relationships, and docking studies of N-phenylarylformamide derivatives (PAFAs) as non-nucleoside HIV reverse transcriptase inhibitors
  作者：Xiao-Dong Ma、Qiu-Qin He、Xuan Zhang、Shi-Qiong Yang、Liu-Meng Yang、Shuang-Xi Gu、Yong-Tang Zheng、Fen-Er Chen、Hui-Fang Dai

  DOI：10.1016/j.ejmech.2012.03.032

  日期：2012.12

  A series of N-phenylarylformamide derivatives (PAFAs) with anti-wild-type HIV-1 activity (EC50 values) ranging from 0.3 nM to 5.1 nM and therapeutic index (TI) ranging from 10 616 to 271 000 were identified as novel non-nucleoside reverse transcriptase inhibitors. Among them, compound 13g (EC50 = 0.30 nM, TI = 184 578), 131 (EC50 = 0.37 nM, TI = 212 819), 13m (EC50 = 0.32 nM, TI = 260 617) and 13r (EC50 = 0.27 nM, TI = 271 000) displayed the highest activity against this type virus nearly as potent as lead compound GW678248. Moreover, all of them were also active to inhibit the double mutant strain A(17) (K103N + Y181C) with EC50 values of 0.29 mu M, 0.14 mu M, 0.10 mu M and 0.27 mu M, respectively. In particular, compound 13m, which showed broad-spectrum anti-HIV activity, was also effective to inhibit the HIV-2 ROD replication within 4.37 mu M concentration. (C) 2012 Elsevier Masson SAS. All rights reserved.