(1S,2S,6R,8S)-4-((S)-1-Chloro-propyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane | 319010-99-6

• 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: (1S,2S,6R,8S)-4-((S)-1-Chloro-propyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane
• 英文别名: (1S,2S,6R,8S)-4-[(1S)-1-chloropropyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 319010-99-6
• 化学式: C₁₃H₂₂BClO₂
• 分子量: 256.58
• InChiKey: CVZWPTBKAXOTDQ-ONYIWYLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  17
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R,8S)-4-((S)-1-Chloro-propyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 生成
  参考文献：
  名称：

  Identification of a potent and rapidly reversible inhibitor of the 20S-proteasome

  摘要：

  Synthesis and in vitro characterization of novel, lactam boronic acid based, selective, and rapidly reversible inhibitor 14 of the 20S-proteasome is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.084
• 作为产物：
  描述：

  在 zinc(II) chloride 作用下， 反应 16.0h， 生成 (1S,2S,6R,8S)-4-((S)-1-Chloro-propyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane
  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

文献信息

• P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease
  作者：E.Scott Priestley、Indawati De Lucca、Bahman Ghavimi、Susan Erickson-Viitanen、Carl P. Decicco

  DOI：10.1016/s0960-894x(02)00682-0

  日期：2002.11

  A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.