4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone | 151091-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone
• 英文别名: 4-(4-benzoylpiperidin-1-yl)-1-(4-(tert-butyl)phenyl)butan-1-one；KSC-352-055；4-(4-benzoylpiperidin-1-yl)-1-(4-tert-butylphenyl)butan-1-one
• CAS: 151091-52-0
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: CMWJRFYIYVVAIA-UHFFFAOYSA-N

物化性质

• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 3.0h， 以76%的产率得到1-<4-<4-(1,1-dimethylethyl)phenyl>-4-hydroxybutyl>-α-phenyl-4-piperidinomethanol
  参考文献：
  名称：

  METHODS AND COMPOSITIONS FOR TREATING INFECTION

  摘要：

  本文提供了用于治疗或预防感染的组合物和方法。

  公开号：

  US20150238473A1
• 作为产物：
  描述：

  4'-叔丁基-4-氯丁酰苯 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone
  参考文献：
  名称：

  Structure-activity relationships within a series of analogues of the histamine H1-antagonist terfenadine

  摘要：

  A number of terfenadine derivatives including terfenadine enantiomers were synthesized and tested for histamine H-1-receptor affinity. No significant differences, in H-1 activity were found between terfenadine enantiomers. Qualitative structure-activity relationship studies identified the alpha,alpha-diphenyl-4-piperidinomethanol moiety as the pharmacophore for the H-1 activity of this group of compounds. The major role of die phenylbutanol moiety in terfenadine seems to be preventing the compound from crossing the blood-brain barrier.

  DOI：

  10.1016/0223-5234(93)90009-4

文献信息

• Methods and compositions for treating infection
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US10004701B2

  公开（公告）日：2018-06-26

  Provided herein are compositions and methods for treating or preventing infection.

  本文提供了用于治疗或预防感染的组合物和方法。
• 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.