(+)-pinanediol (1R)-1-amino-2-methylpropane-1-boronate | 94242-80-5

• 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
• 英文名称: (+)-pinanediol (1R)-1-amino-2-methylpropane-1-boronate
• 英文别名: (R)-2-Methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propan-1-amine；(1R)-2-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]propan-1-amine
• CAS: 94242-80-5
• 化学式: C₁₄H₂₆BNO₂
• 分子量: 251.177
• InChiKey: UXOSNRCNFXNKSR-HNRZYHPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  (+)-pinanediol (1R)-1-amino-2-methylpropane-1-boronate 、 N-[(1,1-二甲基乙氧基)羰基]-L-缬氨酰-L-脯氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以27.04 g的产率得到tert-butyl ((S)-3-methyl-1-((S)-2-(((R)-2-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propyl)carbamoyl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate
  参考文献：
  名称：

  ELASTASE INHIBITOR PRODRUG AND USE THEREOF

  摘要：

  The present disclosure provides an elastase inhibitor prodrug and use thereof, being a compound of formula I or a pharmaceutically acceptable salt, ester, isomer or solvate thereof, prodrugs or isotopically labeled compound. Compared with the compound 52 (control example) in WO 2018/175173 A1, the compound disclosed herein has the advantages of high pulmonary exposure and long half-life. The prodrugs of the present disclosure significantly increase the concentration and residence time of the active compound (control example) in the lungs with significant improvements in pharmacokinetics in vivo compared to the control example.

  公开号：

  US20230107378A1
• 作为产物：
  描述：

  (+)-pinanediol (1R)-1-(N,N-bis(trimethylsilyl)amino)-2-methylpropaneboronate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (+)-pinanediol (1R)-1-amino-2-methylpropane-1-boronate
  参考文献：
  名称：

  Characterization of d-boroAla as a Novel Broad-Spectrum Antibacterial Agent Targeting d-Ala-d-Ala Ligase

  摘要：

  d‐boroAla was previously characterized as an inhibitor of bacterial alanine racemase and d‐Ala‐d‐Ala ligase enzymes (Biochemistry, 28, 1989, 3541). In this study, d‐boroAla was identified and characterized as an antibacterial agent. d‐boroAla has activity against both Gram‐positive and Gram‐negative organisms, with minimal inhibitory concentrations down to 8 μg / mL. A structure–function study on the alkyl side chain (NH2‐CHR‐B(OR’)2) revealed that d‐boroAla is the most effective agent in a series including boroGly, d‐boroHomoAla, and d‐boroVal. l‐boroAla was much less active, and N‐acetylation completely abolished activity. An LC‐MS / MS assay was used to demonstrate that d‐boroAla exerts its antibacterial activity by inhibition of d‐Ala‐d‐Ala ligase. d‐boroAla is bactericidal at 1× minimal inhibitory concentration against Staphylococcus aureus and Bacillus subtilis, which each encode one copy of d‐Ala‐d‐Ala ligase, and at 4× minimal inhibitory concentration against Escherichia coli and Salmonella enterica serovar Typhimurium, which each encode two copies of d‐Ala‐d‐Ala ligase. d‐boroAla demonstrated a frequency of resistance of 8 × 10−8 at 4× minimal inhibitory concentration in S. aureus. These results demonstrate that d‐boroAla has promising antibacterial activity and could serve as the lead agent in a new class of d‐Ala‐d‐Ala ligase targeted antibacterial agents. This study also demonstrates d‐boroAla as a possible probe for d‐Ala‐d‐Ala ligase function.

  DOI：

  10.1111/j.1747-0285.2011.01210.x