4-(2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl)-2-fluoropyridine | 1364564-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl)-2-fluoropyridine
• 英文别名: 4-[2-tert-butyl-4-(6-methoxy-2-naphthyl)-1H-imidazol-5-yl]-2-fluoro-pyridine；4-[2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl]-2-fluoropyridine
• CAS: 1364564-14-6
• 化学式: C₂₃H₂₂FN₃O
• 分子量: 375.446
• InChiKey: RCCOGDKAINQSEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl)-2-fluoropyridine 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以91%的产率得到4-(2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl)pyridin-2(5H)-one
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h
• 作为产物：
  描述：

  ethyl 6-methoxy-2-naphthoate 在 ammonium acetate 、 氢溴酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 正丁醇 为溶剂， 反应 6.25h， 生成 4-(2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl)-2-fluoropyridine
  参考文献：
  名称：

  Trisubstituted Imidazoles as Mycobacterium tuberculosis Glutamine Synthetase Inhibitors

  摘要：

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.

  DOI：

  10.1021/jm201212h

文献信息

• Trisubstituted Imidazoles as <i>Mycobacterium tuberculosis</i> Glutamine Synthetase Inhibitors
  作者：Johan Gising、Mikael T. Nilsson、Luke R. Odell、Samir Yahiaoui、Martin Lindh、Harini Iyer、Achyut M. Sinha、Bachally R. Srinivasa、Mats Larhed、Sherry L. Mowbray、Anders Karlén

  DOI：10.1021/jm201212h

  日期：2012.3.22

  Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore one of these classes, the 2-tert-butyl-4,5-diarylimidazoles, and present the design, synthesis, and X-ray crystallographic studies leading to the identification of MtGS inhibitors with submicromolar IC(50) values and promising antituberculosis MIC values.