曲尼嗪 | 82190-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 曲尼嗪
• 英文名称: 4-(4-benzhydrylpiperazin-1-yl)-1-(4-(tert-butyl)phenyl)-butan-1-ol
• 英文别名: Trenizine；4-(4-benzhydrylpiperazin-1-yl)-1-(4-tert-butylphenyl)butan-1-ol
• CAS: 82190-93-0
• 化学式: C₃₁H₄₀N₂O
• 分子量: 456.671
• InChiKey: DCWPQKGBKYLNRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯氯甲烷 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙腈 、 丁酮 为溶剂， 反应 37.0h， 生成 曲尼嗪
  参考文献：
  名称：

  Repurposing the Antihistamine Terfenadine for Antimicrobial Activity against Staphylococcus aureus

  摘要：

  Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.

  DOI：

  10.1021/jm5010682

文献信息

• Repurposing the Antihistamine Terfenadine for Antimicrobial Activity against <i>Staphylococcus aureus</i>
  作者：Jessamyn I. Perlmutter、Lauren T. Forbes、Damian J. Krysan、Katherine Ebsworth-Mojica、Jennifer M. Colquhoun、Jenna L. Wang、Paul M. Dunman、Daniel P. Flaherty

  DOI：10.1021/jm5010682

  日期：2014.10.23

  Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.