(ALPHAR,3AS,4S,6S,7AR)-ALPHA-乙基六氢-3A,5,5-三甲基-4,6-甲桥-1,3,2-苯并二氧杂硼杂环戊烯-2-甲胺 | 208521-42-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (ALPHAR,3AS,4S,6S,7AR)-ALPHA-乙基六氢-3A,5,5-三甲基-4,6-甲桥-1,3,2-苯并二氧杂硼杂环戊烯-2-甲胺
• 中文别名: (alphaR,3aS,4S,6S,7aR)-alpha-乙基六氢-3a,5,5-三甲基-4,6-甲桥-1,3,2-苯并二氧杂硼杂环戊烯-2-甲胺
• 英文名称: (1R)-1-[(3aS,4S,6S,7aR)-3a,5,5-Trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butan-1-amine
• 英文别名: (1R)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butan-1-amine
• CAS: 208521-42-0
• 化学式: C₁₄H₂₆BNO₂
• 分子量: 251.177
• InChiKey: XEPLXNOYANQXHI-HNRZYHPDSA-N

物化性质

• 沸点：
  287.2±23.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (ALPHAR,3AS,4S,6S,7AR)-ALPHA-乙基六氢-3A,5,5-三甲基-4,6-甲桥-1,3,2-苯并二氧杂硼杂环戊烯-2-甲胺 、 在 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 NMM 为溶剂， 以92%的产率得到[(3R,5S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-5-[[(1R)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butyl]carbamoyl]pyrrolidin-3-yl] 1,3-dihydroisoindole-2-carboxylate
  参考文献：
  名称：

  Synthesis and antiviral activity of HCV NS3/4A peptidomimetic boronic acid inhibitors

  摘要：

  A new series of NS3/4A protease boronic acid inhibitors is described. The compounds show good biochemical potency and cellular activity. The peptidomimetic inhibitors were evaluated against proteases from different HCV genotypes and clinically relevant NS3/4A mutants. Compound 28 displayed subnanomolar to single digit nanomolar potencies in the enzymatic assays and an EC50 of 25 nM in the replicon cell-based assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.017

文献信息

• Synthesis and antiviral activity of HCV NS3/4A peptidomimetic boronic acid inhibitors
  作者：Amogh Boloor、Denise Hanway、Maria Joshi、David T. Winn、Gabriel Mendez、Marlena Walls、Ping Wei、Fuxin Qian、Xiaoli Zhang、Yuliang Zhang、Michael E. Hepperle、Xinqiang Li、David A. Campbell、Juan M. Betancort

  DOI：10.1016/j.bmcl.2009.08.017

  日期：2009.10

  A new series of NS3/4A protease boronic acid inhibitors is described. The compounds show good biochemical potency and cellular activity. The peptidomimetic inhibitors were evaluated against proteases from different HCV genotypes and clinically relevant NS3/4A mutants. Compound 28 displayed subnanomolar to single digit nanomolar potencies in the enzymatic assays and an EC50 of 25 nM in the replicon cell-based assay. (C) 2009 Elsevier Ltd. All rights reserved.