(3-Fluorophenyl)vinylborinic acid quinolin-8-yl ester | 871817-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3-Fluorophenyl)vinylborinic acid quinolin-8-yl ester
• 英文别名: Borinic acid, ethenyl(3-fluorophenyl)-, 8-quinolinyl ester；ethenyl-(3-fluorophenyl)-quinolin-8-yloxyborane
• CAS: 871817-01-5
• 化学式: C₁₇H₁₃BFNO
• 分子量: 277.106
• InChiKey: SFWMDIFLSZPOKW-UHFFFAOYSA-N

物化性质

• 沸点：
  384.0±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-fluorophenyl)[1,3,2]dioxaborolane 以 四氢呋喃 、 乙醇 为溶剂， 生成 (3-Fluorophenyl)vinylborinic acid quinolin-8-yl ester
  参考文献：
  名称：

  Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH

  摘要：

  As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.

  DOI：

  10.1021/jm050676a

文献信息

• Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH
  作者：Stephen J. Benkovic、Stephen J. Baker、M. R. K. Alley、Youn-Hi Woo、Yong-Kang Zhang、Tsutomu Akama、Weimin Mao、Justin Baboval、P. T. Ravi Rajagopalan、Mark Wall、Lyn Sue Kahng、Ali Tavassoli、Lucy Shapiro

  DOI：10.1021/jm050676a

  日期：2005.11.1

  As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.