1-ethyl-7-(trifluoromethyl)-5H-1,3,5-benzotriazepine-2,4-dione | 1329991-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-ethyl-7-(trifluoromethyl)-5H-1,3,5-benzotriazepine-2,4-dione
• CAS: 1329991-40-3
• 化学式: C₁₁H₁₀F₃N₃O₂
• 分子量: 273.215
• InChiKey: MHCUEOOABBLUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethyl-7-(trifluoromethyl)-5H-1,3,5-benzotriazepine-2,4-dione 在 吡啶 、 二(三叔丁基膦)钯 、 copper diacetate potassium phosphate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 1-Ethyl-5-phenyl-3-[(2-pyridin-4-ylphenyl)methyl]-7-(trifluoromethyl)-1,3,5-benzotriazepine-2,4-dione
  参考文献：
  名称：

  [EN] DERIVATIVES OF L-PLIENYL-1.5-DILIYDIO-BENZO[B] [1.4]DIAZEPINE-2.4-DIONE AS INHIBITORS OF HIV REPLICATION
  [FR] DÉRIVÉS DE 1-PHÉNYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZÉPINE-2.4-DIONE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIH

  摘要：

  公开号：

  WO2011100838A9
• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 在 palladium 10% on activated carbon 甲酸 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1-ethyl-7-(trifluoromethyl)-5H-1,3,5-benzotriazepine-2,4-dione
  参考文献：
  名称：

  [EN] DERIVATIVES OF L-PLIENYL-1.5-DILIYDIO-BENZO[B] [1.4]DIAZEPINE-2.4-DIONE AS INHIBITORS OF HIV REPLICATION
  [FR] DÉRIVÉS DE 1-PHÉNYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZÉPINE-2.4-DIONE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIH

  摘要：

  公开号：

  WO2011100838A9

文献信息

• Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 1: Addressing configurational instability through scaffold modification
  作者：Lee D. Fader、Serge Landry、Sébastien Morin、Stephen H. Kawai、Yves Bousquet、Oliver Hucke、Nathalie Goudreau、Christopher T. Lemke、Pierre Bonneau、Steve Titolo、Stephen Mason、Bruno Simoneau

  DOI：10.1016/j.bmcl.2013.03.073

  日期：2013.6

  The optimization of a 1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly that possess a labile stereocenter at C3 is described. Quaternization of the C3 position of compound 1 in order to prevent racemization gave compound 2, which was inactive in our capsid disassembly assay. A likely explanation for this finding was revealed by in silico analysis predicting a dramatic increase in energy of the bioactive conformation upon quaternization of the C3 position. Replacement of the C3 of the diazepine ring with a nitrogen atom to give the 1,5-dihydro-benzo[f][1,3,5]-triazepine-2,4-dione analog 4 was well tolerated. Introduction of a rigid spirocyclic system at the C3 position gave configurationally stable 1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione analog 5, which was able to access the bioactive conformation without a severe energetic penalty and inhibit capsid assembly. Preliminary structure-activity relationships (SAR) and X-ray crystallographic data show that knowledge from the 1,5-dihydrobenzo[ b][1,4] diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly can be transferred to these new scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.
• [EN] DERIVATIVES OF 1-PHENYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZEPINE-2.4-DIONE AS INHIBITORS OF HIV REPLICATION<br/>[FR] DÉRIVÉS DE 1-PHÉNYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZÉPINE-2.4-DIONE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIH
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011100838A1

  公开（公告）日：2011-08-25

  Compounds of formula (I) wherein m, R1, R2, R3, X and Y are defined herein, are useful as inhibitors of HIV replication.