1-Ethyl-3-(4-hydroxy-3-methoxyphenyl)-5-phenyl-7-(trifluoromethyl)-1,5-benzodiazepine-2,4-dione | 1329989-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 1-Ethyl-3-(4-hydroxy-3-methoxyphenyl)-5-phenyl-7-(trifluoromethyl)-1,5-benzodiazepine-2,4-dione
• 英文别名: 1-ethyl-3-(4-hydroxy-3-methoxyphenyl)-5-phenyl-7-(trifluoromethyl)-1,5-benzodiazepine-2,4-dione
• CAS: 1329989-01-6
• 化学式: C₂₅H₂₁F₃N₂O₄
• 分子量: 470.448
• InChiKey: XICDDEMZRGQJJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  高香兰酸乙酯 在 吡啶 、 copper diacetate 、 sodium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 1-Ethyl-3-(4-hydroxy-3-methoxyphenyl)-5-phenyl-7-(trifluoromethyl)-1,5-benzodiazepine-2,4-dione
  参考文献：
  名称：

  Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 2: Structure–activity relationships (SAR) of the C3-phenyl moiety

  摘要：

  Detailed structure-activity relationships of the C3-phenyl moiety that allow for the optimization of antiviral potency of a series of 1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione inhibitors of HIV capsid (CA) assembly are described. Combination of favorable substitutions gave additive SAR and allowed for the identification of the most potent compound in the series, analog 27. Productive SAR also transferred to the benzotriazepine and spirobenzodiazepine scaffolds, providing a solution to the labile stereocenter at the C3 position. The molecular basis of how compound 27 inhibits mature CA assembly is rationalized using high-resolution structural information. Our understanding of how compound 27 may inhibit immature Gag assembly is also discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.074

文献信息

• Derivatives of 1-Phenyl-1,5-Dihydro-Benzo[B] [1,4]Diazepine-2,4-Dione as Inhibitors of HIV Replication
  申请人：Simoneau Bruno

  公开号：US20130150350A1

  公开（公告）日：2013-06-13

  Compounds of formula (I) wherein m, R 1 , R 2 , R 3 , X and Y are defined herein, are useful as inhibitors of HIV replication.
• Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 2: Structure–activity relationships (SAR) of the C3-phenyl moiety
  作者：Lee D. Fader、Serge Landry、Sylvie Goulet、Sébastien Morin、Stephen H. Kawai、Yves Bousquet、Isabelle Dion、Oliver Hucke、Nathalie Goudreau、Christopher T. Lemke、Jean Rancourt、Pierre Bonneau、Steve Titolo、Ma’an Amad、Michel Garneau、Jianmin Duan、Stephen Mason、Bruno Simoneau

  DOI：10.1016/j.bmcl.2013.03.074

  日期：2013.6

  Detailed structure-activity relationships of the C3-phenyl moiety that allow for the optimization of antiviral potency of a series of 1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione inhibitors of HIV capsid (CA) assembly are described. Combination of favorable substitutions gave additive SAR and allowed for the identification of the most potent compound in the series, analog 27. Productive SAR also transferred to the benzotriazepine and spirobenzodiazepine scaffolds, providing a solution to the labile stereocenter at the C3 position. The molecular basis of how compound 27 inhibits mature CA assembly is rationalized using high-resolution structural information. Our understanding of how compound 27 may inhibit immature Gag assembly is also discussed. (C) 2013 Elsevier Ltd. All rights reserved.