5-fluoro-2-methyl-4'-nitrobenzophenone | 1043425-46-2

• 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: 5-fluoro-2-methyl-4'-nitrobenzophenone
• 英文别名: (5-Fluoro-2-methylphenyl)(4-nitrophenyl)methanone；(5-fluoro-2-methylphenyl)-(4-nitrophenyl)methanone
• CAS: 1043425-46-2
• 化学式: C₁₄H₁₀FNO₃
• 分子量: 259.237
• InChiKey: OEIQRGCVDOEAAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-methyl-4'-nitrobenzophenone 在 吡啶 、 potassium permanganate 作用下， 以 水 为溶剂， 反应 144.0h， 生成 2-(4-nitrobenzoyl)-4-fluorobenzoic acid
  参考文献：
  名称：

  Ethyl 8-Fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate as Novel, Highly Potent, and Safe Antianxiety Agent

  摘要：

  Ethyl 8-fluoro-6-(4-nitrophenyl)- and ethyl 8-fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine 3-carboxylate 6 and 7 were synthesized as central benzodiazepine receptor (CBR) ligands and tested for their ability to displace [3 H]flumazenil from bovine and human cortical brain membranes. Both compounds showed high affinity for bovine and human CBR. In particular, compound 7 emerged as the most interesting compound, having a partial agonist profile in vitro while possessing useful activity in various animal models of anxiety. In accordance with its partial agonist profile, compound 7 was devoid of typical benzodiazepine, side effects. The homology model of the GABA(A) receptor developed by Cromer et al. was used to assess the binding modes of ligands 6 and 7. From our docking results, the partial agonist activity elicited by compound 7 is likely to be due to the 3'-nitro substituent, which is in the appropriate position to interact with Thr193 of the gamma(2)-subunit by means of a hydrogen bond.

  DOI：

  10.1021/jm8002944
• 作为产物：
  描述：

  5-fluoro-2-methyl-4'-nitrobenzhydrol 在 吡啶 、 四丁基高锰酸胺盐 作用下， 反应 0.33h， 生成 5-fluoro-2-methyl-4'-nitrobenzophenone
  参考文献：
  名称：

  Ethyl 8-Fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate as Novel, Highly Potent, and Safe Antianxiety Agent

  摘要：

  Ethyl 8-fluoro-6-(4-nitrophenyl)- and ethyl 8-fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine 3-carboxylate 6 and 7 were synthesized as central benzodiazepine receptor (CBR) ligands and tested for their ability to displace [3 H]flumazenil from bovine and human cortical brain membranes. Both compounds showed high affinity for bovine and human CBR. In particular, compound 7 emerged as the most interesting compound, having a partial agonist profile in vitro while possessing useful activity in various animal models of anxiety. In accordance with its partial agonist profile, compound 7 was devoid of typical benzodiazepine, side effects. The homology model of the GABA(A) receptor developed by Cromer et al. was used to assess the binding modes of ligands 6 and 7. From our docking results, the partial agonist activity elicited by compound 7 is likely to be due to the 3'-nitro substituent, which is in the appropriate position to interact with Thr193 of the gamma(2)-subunit by means of a hydrogen bond.

  DOI：

  10.1021/jm8002944

文献信息

• Ethyl 8-Fluoro-6-(3-nitrophenyl)-4<i>H</i>-imidazo[1,5-<i>a</i>][1,4]benzodiazepine-3-carboxylate as Novel, Highly Potent, and Safe Antianxiety Agent
  作者：Maurizio Anzini、Carlo Braile、Salvatore Valenti、Andrea Cappelli、Salvatore Vomero、Luciana Marinelli、Vittorio Limongelli、Ettore Novellino、Laura Betti、Gino Giannaccini、Antonio Lucacchini、Carla Ghelardini、Monica Norcini、Francesco Makovec、Gianluca Giorgi、R. Ian Fryer

  DOI：10.1021/jm8002944

  日期：2008.8.1

  Ethyl 8-fluoro-6-(4-nitrophenyl)- and ethyl 8-fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine 3-carboxylate 6 and 7 were synthesized as central benzodiazepine receptor (CBR) ligands and tested for their ability to displace [3 H]flumazenil from bovine and human cortical brain membranes. Both compounds showed high affinity for bovine and human CBR. In particular, compound 7 emerged as the most interesting compound, having a partial agonist profile in vitro while possessing useful activity in various animal models of anxiety. In accordance with its partial agonist profile, compound 7 was devoid of typical benzodiazepine, side effects. The homology model of the GABA(A) receptor developed by Cromer et al. was used to assess the binding modes of ligands 6 and 7. From our docking results, the partial agonist activity elicited by compound 7 is likely to be due to the 3'-nitro substituent, which is in the appropriate position to interact with Thr193 of the gamma(2)-subunit by means of a hydrogen bond.