Ethyl 3-[(4-methoxyphenyl)methyl]-5-[methyl-(2,2,2-trifluoroacetyl)amino]imidazole-4-carboxylate | 1267635-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Ethyl 3-[(4-methoxyphenyl)methyl]-5-[methyl-(2,2,2-trifluoroacetyl)amino]imidazole-4-carboxylate
• 英文别名: ethyl 3-[(4-methoxyphenyl)methyl]-5-[methyl-(2,2,2-trifluoroacetyl)amino]imidazole-4-carboxylate
• CAS: 1267635-74-4
• 化学式: C₁₇H₁₈F₃N₃O₄
• 分子量: 385.343
• InChiKey: IWBHSHKPGFUVAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[(4-methoxyphenyl)methyl]-5-[methyl-(2,2,2-trifluoroacetyl)amino]imidazole-4-carboxylate 在 吡啶 、 三氟甲磺酸 、 sodium ethanolate 、 copper diacetate 、 sodium hexamethyldisilazane 、 铁粉 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 7-chloro-10-methyl-5-phenyl-3H-imidazo[4,5-c][1,5]benzodiazepin-4-one
  参考文献：
  名称：

  Discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly

  摘要：

  The discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly is described. Synthesis of analogs of the 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hit established structure-activity relationships. Replacement of the enamine functionality of the hit series with either an imidazole or a pyrazole ring led to compounds that inhibited both capsid assembly and reverse transcriptase. Optimization of the bicyclic benzodiazepine scaffold to include a 3-phenyl substituent led to lead compound 48, a pure capsid assembly inhibitor with improved antiviral activity. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.131
• 作为产物：
  描述：

  1-(4-甲氧基苄基)-4-氨基-1H-咪唑-5-羧酸乙酯 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 Ethyl 3-[(4-methoxyphenyl)methyl]-5-[methyl-(2,2,2-trifluoroacetyl)amino]imidazole-4-carboxylate
  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

• [EN] DERIVATIVES OF L-PLIENYL-1.5-DILIYDIO-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：WO2011100838A9

  公开（公告）日：2012-12-27
• 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.
• Discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly
  作者：Lee D. Fader、Richard Bethell、Pierre Bonneau、Michael Bös、Yves Bousquet、Michael G. Cordingley、René Coulombe、Patrick Deroy、Anne-Marie Faucher、Alexandre Gagnon、Nathalie Goudreau、Chantal Grand-Maître、Ingrid Guse、Oliver Hucke、Stephen H. Kawai、Jean-Eric Lacoste、Serge Landry、Christopher T. Lemke、Eric Malenfant、Stephen Mason、Sébastien Morin、Jeff O’Meara、Bruno Simoneau、Steve Titolo、Christiane Yoakim

  DOI：10.1016/j.bmcl.2010.10.131

  日期：2011.1

  The discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly is described. Synthesis of analogs of the 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hit established structure-activity relationships. Replacement of the enamine functionality of the hit series with either an imidazole or a pyrazole ring led to compounds that inhibited both capsid assembly and reverse transcriptase. Optimization of the bicyclic benzodiazepine scaffold to include a 3-phenyl substituent led to lead compound 48, a pure capsid assembly inhibitor with improved antiviral activity. (c) 2010 Elsevier Ltd. All rights reserved.