N-(2-nitrophenyl)-2-[3-(2,4,6-trimethylphenyl)imidazo[4,5-b]pyridin-2-yl]sulfanyl-acetamide | 1383786-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-nitrophenyl)-2-[3-(2,4,6-trimethylphenyl)imidazo[4,5-b]pyridin-2-yl]sulfanyl-acetamide
• 英文别名: N-(2-nitrophenyl)-2-[3-(2,4,6-trimethylphenyl)imidazo[4,5-b]pyridin-2-yl]sulfanylacetamide
• CAS: 1383786-81-9
• 化学式: C₂₃H₂₁N₅O₃S
• 分子量: 447.517
• InChiKey: AHMMXCOCBJLJLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2,4,6-trimethylphenyl)amino-3-nitropyridine 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 22.0h， 生成 N-(2-nitrophenyl)-2-[3-(2,4,6-trimethylphenyl)imidazo[4,5-b]pyridin-2-yl]sulfanyl-acetamide
  参考文献：
  名称：

  Arylazolyl(azinyl)thioacetanilides. Part 10: Design, synthesis and biological evaluation of novel substituted imidazopyridinylthioacetanilides as potent HIV-1 inhibitors

  摘要：

  In continuation of our efforts toward the discovery of potent HIV-1 NNRTIs with novel structures, we have employed a scaffold hopping strategy to explore the chemically diversed space of bioactive compounds. The original arylazolylthioacetanilide platform was replaced with different imidazopyridinylthioacetanilide scaffolds to yield the optimal pharmacophore moieties in order to generate novel NNRTIs with desirable potency. Some of the new compounds proved able to inhibit HIV-1 replication in the low micromolar range. In particular, compound 5b16 displayed the most potent anti-HIV-1 activity (EC50 = 0.21 +/- 0.06 mu M), inhibiting HIV-1 IIIB replication in MT-4 cells more effectively than dideoxycytidine (EC50 = 1.4 +/- 0.1 mu M) and similarly with nevirapine (EC50 = 0.20 +/- 0.10 mu M). Preliminary structure-activity relationship (SAR) of the newly synthesized congeners is discussed, and molecular modeling study is performed to rationalize the SAR conclusions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.026

文献信息

• Arylazolyl(azinyl)thioacetanilides. Part 10: Design, synthesis and biological evaluation of novel substituted imidazopyridinylthioacetanilides as potent HIV-1 inhibitors
  作者：Xiao Li、Peng Zhan、Hong Liu、Dongyue Li、Liu Wang、Xuwang Chen、Huiqing Liu、Christophe Pannecouque、Jan Balzarini、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.bmc.2012.07.026

  日期：2012.9

  In continuation of our efforts toward the discovery of potent HIV-1 NNRTIs with novel structures, we have employed a scaffold hopping strategy to explore the chemically diversed space of bioactive compounds. The original arylazolylthioacetanilide platform was replaced with different imidazopyridinylthioacetanilide scaffolds to yield the optimal pharmacophore moieties in order to generate novel NNRTIs with desirable potency. Some of the new compounds proved able to inhibit HIV-1 replication in the low micromolar range. In particular, compound 5b16 displayed the most potent anti-HIV-1 activity (EC50 = 0.21 +/- 0.06 mu M), inhibiting HIV-1 IIIB replication in MT-4 cells more effectively than dideoxycytidine (EC50 = 1.4 +/- 0.1 mu M) and similarly with nevirapine (EC50 = 0.20 +/- 0.10 mu M). Preliminary structure-activity relationship (SAR) of the newly synthesized congeners is discussed, and molecular modeling study is performed to rationalize the SAR conclusions. (C) 2012 Elsevier Ltd. All rights reserved.