benzyl (6S,8R)-6-(anilinocarbonyl)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl[3-(trifluoromethyl)benzyl]carbamate | 437761-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (6S,8R)-6-(anilinocarbonyl)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl[3-(trifluoromethyl)benzyl]carbamate
• 英文别名: (6S)-N-Phenyl-3-[3-(trifluoromethyl)benzyl(benzyloxycarbonyl)amino]-4-oxo-8beta-azido-8-methyl-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6alpha-carboxamide；benzyl N-[(6S,8R)-8-azido-8-methyl-4-oxo-6-(phenylcarbamoyl)-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-[[3-(trifluoromethyl)phenyl]methyl]carbamate
• CAS: 437761-06-3
• 化学式: C₃₁H₂₆F₃N₇O₄
• 分子量: 617.587
• InChiKey: YNUSVJSOGDSAEZ-QABMSTFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (6S,8R)-6-(anilinocarbonyl)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl[3-(trifluoromethyl)benzyl]carbamate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 双氧水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (6S,8R)-8-Amino-8-methyl-4-oxo-3-(3-trifluoromethyl-benzylamino)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid [(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propyl]-amide
  参考文献：
  名称：

  Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors

  摘要：

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00022-2
• 作为产物：
  描述：

  (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid 在 N-羟基-7-氮杂苯并三氮唑 、 2,4,6-三异丙基苯磺酰叠氮化物 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 生成 benzyl (6S,8R)-6-(anilinocarbonyl)-8-azido-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl[3-(trifluoromethyl)benzyl]carbamate
  参考文献：
  名称：

  Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors

  摘要：

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00022-2

文献信息

• Inhibitors of hepatitis C virus NS3 protease
  申请人：——

  公开号：US20030064962A1

  公开（公告）日：2003-04-03

  The present invention relates generally to a novel class of pyrimidinones of Formula (I): 1 that are useful as serine protease inhibitors, and more particularly as Hepatitis C virus NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

  本发明一般涉及一种新型的嘧啶酮类化合物，具有如下式（I）所示的结构，这些化合物可用作丝氨酸蛋白酶抑制剂，更具体地作为丙型肝炎病毒NS3蛋白酶抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些药物的方法。
• Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors
  作者：Peter W Glunz、Brent D Douty、Carl P Decicco

  DOI：10.1016/s0960-894x(03)00022-2

  日期：2003.3

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.