7-chloro-1-ethyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione | 22316-25-2

• 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: 7-chloro-1-ethyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione
• 英文别名: 1-phenyl 5-ethyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3H-1,5-benzodiazepine；7-Chloro-1-ethyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione；7-chloro-1-ethyl-5-phenyl-1,5-benzodiazepine-2,4-dione
• CAS: 22316-25-2
• 化学式: C₁₇H₁₅ClN₂O₂
• 分子量: 314.771
• InChiKey: GWVJSTVUWPHUTL-UHFFFAOYSA-N

物化性质

• 沸点：
  642.5±55.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-1-ethyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 生成 7-chloro-1-ethyl-3-[(2-methoxyethylamino)methylidene]-5-phenyl-1,5-benzodiazepine-2,4-dione
  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：

  5-氯-2-(乙胺基)苯胺 在 copper diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-chloro-1-ethyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione
  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

文献信息

• US3984398A
  申请人：——

  公开号：US3984398A

  公开（公告）日：1976-10-05
• US4001408A
  申请人：——

  公开号：US4001408A

  公开（公告）日：1977-01-04
• US4138572A
  申请人：——

  公开号：US4138572A

  公开（公告）日：1979-02-06
• 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.