N-(3-bromophenyl)-3-nitrobenzamide | 69754-51-4

• 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-(3-bromophenyl)-3-nitrobenzamide
• 英文别名: 3-Nitro-benzoesaeure-<3-brom-anilid>
• CAS: 69754-51-4
• 化学式: C₁₃H₉BrN₂O₃
• mdl: MFCD01010602
• 分子量: 321.13
• InChiKey: JNAUOCDRHXZHDA-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±27.0 °C(Predicted)
• 密度：
  1.635±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-bromophenyl)-3-nitrobenzamide 在 tin(II) chloride dihdyrate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.5h， 生成 N-(3-bromophenyl)-3-propionamidobenzamide
  参考文献：
  名称：

  Tri- and Tetrasubstituted Pyridinylimidazoles as Covalent Inhibitors of c-Jun N-Terminal Kinase 3

  摘要：

  The concept of covalent inhibition of c-Jun N-terminal kinase 3 (JNK3) was successfully transferred to our well validated pyridinylimidazole scaffold varying several structural features in order to deduce crucial structure-activity relationships. Joint targeting of the hydrophobic region I and methylation of imidazole-N1 position increased the activity and reduced the number of off-targets. The most promising covalent inhibitor, the tetrasubstituted imidazole 3-acrylamido-N-(4-((4-(4-(4-fluoropheny1)-1-methyl-2-(methylthio)-1H-imidazol-S-yl)pyridin-2-yl)amino)phenyl)benzamide (7) inhibits the JNK3 in the subnanomolar range (IC50 = 0.3 nM), shows high metabolic stability in human liver microsomes, and displays excellent selectivity in a screening against a panel of 410 kinases. Covalent bond formation to Cys-154 was confirmed by incubation of the inhibitors with wild-type JNK3 and JNK3-C154A mutant followed by mass spectrometry.

  DOI：

  10.1021/acs.jmedchem.6b01180
• 作为产物：
  描述：

  间溴苯胺 、 间硝基苯甲酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到N-(3-bromophenyl)-3-nitrobenzamide
  参考文献：
  名称：

  Tri- and Tetrasubstituted Pyridinylimidazoles as Covalent Inhibitors of c-Jun N-Terminal Kinase 3

  摘要：

  The concept of covalent inhibition of c-Jun N-terminal kinase 3 (JNK3) was successfully transferred to our well validated pyridinylimidazole scaffold varying several structural features in order to deduce crucial structure-activity relationships. Joint targeting of the hydrophobic region I and methylation of imidazole-N1 position increased the activity and reduced the number of off-targets. The most promising covalent inhibitor, the tetrasubstituted imidazole 3-acrylamido-N-(4-((4-(4-(4-fluoropheny1)-1-methyl-2-(methylthio)-1H-imidazol-S-yl)pyridin-2-yl)amino)phenyl)benzamide (7) inhibits the JNK3 in the subnanomolar range (IC50 = 0.3 nM), shows high metabolic stability in human liver microsomes, and displays excellent selectivity in a screening against a panel of 410 kinases. Covalent bond formation to Cys-154 was confirmed by incubation of the inhibitors with wild-type JNK3 and JNK3-C154A mutant followed by mass spectrometry.

  DOI：

  10.1021/acs.jmedchem.6b01180

文献信息

• [EN] AKT3 MODULATORS<br/>[FR] MODULATEURS DE AKT3
  申请人：GEORGIAMUNE LLC

  公开号：WO2021226458A1

  公开（公告）日：2021-11-11

  Compounds of Formula la, lb, or Ic, (Ia); (Ib); or (Ic), are described, where the various substituents are defined herein. The compounds can modulate a property or effect of Akt3 in vitro or in vivo, and can also be used, individually or in combination with other agents, in the prevention or treatment of a variety of conditions. Methods for synthesizing the compounds are described. Pharmaceutical compositions and methods of using these compounds or compositions, individually or in combination with other agents or compositions, in the prevention or treatment of a variety of conditions are also described.

  本文描述了化合物la、lb或Ic的公式(Ia)；(Ib)；或(Ic)，其中各种取代基在此处定义。这些化合物可以在体外或体内调节Akt3的性质或效果，并且还可以单独或与其他药剂结合在预防或治疗各种疾病方面使用。描述了合成这些化合物的方法。还描述了药物组合物和使用这些化合物或组合物的方法，单独或与其他药剂或组合物结合在预防或治疗各种疾病方面。
• Likhomanenko, E. E.; Shpan'ko, I. V.; Litvinenko, L. M., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 12, p. 2341 - 2347
  作者：Likhomanenko, E. E.、Shpan'ko, I. V.、Litvinenko, L. M.、Goncharov, A. N.

  DOI：——

  日期：——
• Tri- and Tetrasubstituted Pyridinylimidazoles as Covalent Inhibitors of c-Jun N-Terminal Kinase 3
  作者：Felix Muth、Ahmed El-Gokha、Francesco Ansideri、Michael Eitel、Eva Döring、Adrian Sievers-Engler、Andreas Lange、Frank M. Boeckler、Michael Lämmerhofer、Pierre Koch、Stefan A. Laufer

  DOI：10.1021/acs.jmedchem.6b01180

  日期：2017.1.26

  The concept of covalent inhibition of c-Jun N-terminal kinase 3 (JNK3) was successfully transferred to our well validated pyridinylimidazole scaffold varying several structural features in order to deduce crucial structure-activity relationships. Joint targeting of the hydrophobic region I and methylation of imidazole-N1 position increased the activity and reduced the number of off-targets. The most promising covalent inhibitor, the tetrasubstituted imidazole 3-acrylamido-N-(4-((4-(4-(4-fluoropheny1)-1-methyl-2-(methylthio)-1H-imidazol-S-yl)pyridin-2-yl)amino)phenyl)benzamide (7) inhibits the JNK3 in the subnanomolar range (IC50 = 0.3 nM), shows high metabolic stability in human liver microsomes, and displays excellent selectivity in a screening against a panel of 410 kinases. Covalent bond formation to Cys-154 was confirmed by incubation of the inhibitors with wild-type JNK3 and JNK3-C154A mutant followed by mass spectrometry.