(6S,8R)-N-{(1R)-1-[(3AS,4S,6S,7AR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]propyl}-8-methyl-4-oxo-8-[(2-toluidinocarbonyl)amino]-3-{[3-(trifluoromethyl)benzyl]amino}-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6S,8R)-N-{(1R)-1-[(3AS,4S,6S,7AR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]propyl}-8-methyl-4-oxo-8-[(2-toluidinocarbonyl)amino]-3-{[3-(trifluoromethyl)benzyl]amino}-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxamide
• 英文别名: (6S,8R)-8-methyl-8-[(2-methylphenyl)carbamoylamino]-4-oxo-3-[[3-(trifluoromethyl)phenyl]methylamino]-N-[(1R)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]propyl]-6,7-dihydropyrrolo[1,2-a]pyrimidine-6-carboxamide
• 化学式: C₃₈H₄₆BF₃N₆O₅
• 分子量: 734.627
• InChiKey: ARZYBAJJJGSANH-IDAKZRBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  53
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  tert-Butyl (6S,8R)-(8-azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-yl)carbonyl(phenyl)carbamate 在 palladium on activated charcoal 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 、 二氯甲烷 为溶剂， 生成 (6S,8R)-N-{(1R)-1-[(3AS,4S,6S,7AR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]propyl}-8-methyl-4-oxo-8-[(2-toluidinocarbonyl)amino]-3-{[3-(trifluoromethyl)benzyl]amino}-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxamide
  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

• 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.