4-(4-Aminophenyl)-8-bromo-1-(2-methoxyethyl)benzofuro[3,2-d]pyrimidin-2-one | 1251588-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-Aminophenyl)-8-bromo-1-(2-methoxyethyl)benzofuro[3,2-d]pyrimidin-2-one
• 英文别名: 4-(4-aminophenyl)-8-bromo-1-(2-methoxyethyl)-[1]benzofuro[3,2-d]pyrimidin-2-one
• CAS: 1251588-31-4
• 化学式: C₁₉H₁₆BrN₃O₃
• 分子量: 414.258
• InChiKey: CXNOQEQFOMNHBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-2-甲基-6-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-异喹啉 、 4-(4-Aminophenyl)-8-bromo-1-(2-methoxyethyl)benzofuro[3,2-d]pyrimidin-2-one 、 乙胺 、 溴乙酰溴 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 、 cesium fluoride 作用下， 以 二氯甲烷 、 四氢呋喃 、 N,N-二甲基甲酰胺 、 1,4-二氧六环 、 水 为溶剂， 以44%的产率得到2-(ethylamino)-N-[4-[1-(2-methoxyethyl)-8-(2-methyl-3,4-dihydro-1H-isoquinolin-6-yl)-2-oxo-benzofuro[3,2-d]pyrimidin-4-yl]phenyl]acetamide
  参考文献：
  名称：

  Identification of benzofurano[3,2-d]pyrimidin-2-ones, a new series of HIV-1 nucleotide-competing reverse transcriptase inhibitors

  摘要：

  Screening of our sample collection led to the identification of a set of benzofurano[3,2-d]pyrimidine-2one hits acting as nucleotide-competing HIV-1 reverse transcriptase inhibitiors (NcRTI). Significant improvement in antiviral potency was achieved when substituents were introduced at positions N1, C4, C7 and C8 on the benzofuranopyrimidone scaffold. The series was optimized from low micromolar enzymatic activity against HIV-1 RT and no antiviral activity to low nanomolar antiviral potency. Further profiling of inhibitor 30 showed promising overall in vitro properties and also demonstrated that its potency was maintained against viruses resistant to the other major classes of HIV-1 RT inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.042
• 作为产物：
  描述：

  (3-Amino-5-bromobenzofuran-2-yl)(4-nitrophenyl)methanone 在 ammonium acetate 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 4-(4-Aminophenyl)-8-bromo-1-(2-methoxyethyl)benzofuro[3,2-d]pyrimidin-2-one
  参考文献：
  名称：

  Identification of benzofurano[3,2-d]pyrimidin-2-ones, a new series of HIV-1 nucleotide-competing reverse transcriptase inhibitors

  摘要：

  Screening of our sample collection led to the identification of a set of benzofurano[3,2-d]pyrimidine-2one hits acting as nucleotide-competing HIV-1 reverse transcriptase inhibitiors (NcRTI). Significant improvement in antiviral potency was achieved when substituents were introduced at positions N1, C4, C7 and C8 on the benzofuranopyrimidone scaffold. The series was optimized from low micromolar enzymatic activity against HIV-1 RT and no antiviral activity to low nanomolar antiviral potency. Further profiling of inhibitor 30 showed promising overall in vitro properties and also demonstrated that its potency was maintained against viruses resistant to the other major classes of HIV-1 RT inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.042

文献信息

• INHIBITORS OF HIV REPLICATION
  申请人：STURINO Claudio

  公开号：US20100261714A1

  公开（公告）日：2010-10-14

  Compounds of formula (I): wherein R 1 , R 2 , A 1 , A 2 , A 3 , A 4 , X and Y are as defined herein, are useful as inhibitors of HIV replication.

  式(I)的化合物： 其中R1、R2、A1、A2、A3、A4、X和Y如本文所定义，可用作HIV复制抑制剂。
• US8349839B2
  申请人：——

  公开号：US8349839B2

  公开（公告）日：2013-01-08
• [EN] INHIBITORS OF HIV REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIH
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010115264A1

  公开（公告）日：2010-10-14

  Compounds of formula (I): wherein R1, R2, A1, A2, A3, A4, X and Y are as defined herein, are useful as inhibitors of HIV replication.
• Identification of benzofurano[3,2-d]pyrimidin-2-ones, a new series of HIV-1 nucleotide-competing reverse transcriptase inhibitors
  作者：Martin Tremblay、Richard C. Bethell、Michael G. Cordingley、Patrick DeRoy、Jianmin Duan、Martin Duplessis、Paul J. Edwards、Anne-Marie Faucher、Ted Halmos、Clint A. James、Cyrille Kuhn、Jean-Éric Lacoste、Louie Lamorte、Steven R. LaPlante、Éric Malenfant、Joannie Minville、Louis Morency、Sébastien Morin、Daniel Rajotte、Patrick Salois、Bruno Simoneau、Sonia Tremblay、Claudio F. Sturino

  DOI：10.1016/j.bmcl.2013.02.042

  日期：2013.5

  Screening of our sample collection led to the identification of a set of benzofurano[3,2-d]pyrimidine-2one hits acting as nucleotide-competing HIV-1 reverse transcriptase inhibitiors (NcRTI). Significant improvement in antiviral potency was achieved when substituents were introduced at positions N1, C4, C7 and C8 on the benzofuranopyrimidone scaffold. The series was optimized from low micromolar enzymatic activity against HIV-1 RT and no antiviral activity to low nanomolar antiviral potency. Further profiling of inhibitor 30 showed promising overall in vitro properties and also demonstrated that its potency was maintained against viruses resistant to the other major classes of HIV-1 RT inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.