3-(4-(hydroxydiphenylmethyl)piperidin-1-yl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-(hydroxydiphenylmethyl)piperidin-1-yl)propan-1-ol
• 英文别名: KSC-367-033；4-(hydroxydiphenylmethyl)-1-piperidinepropanol；3-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]propan-1-ol
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: OLRHCBMEFIAHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-(hydroxydiphenylmethyl)piperidin-1-yl)propan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 (1-(3-((4-(tert-butyl)phenyl)amino)propyl)piperidin-4-yl)diphenylmethanol
  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
• 作为产物：
  描述：

  α,α-二苯基-4-哌啶甲醇 、 3-溴-1-丙醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到3-(4-(hydroxydiphenylmethyl)piperidin-1-yl)propan-1-ol
  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

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。
• US5063235A
  申请人：——

  公开号：US5063235A

  公开（公告）日：1991-11-05
• 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.
• METHODS AND COMPOSITIONS FOR TREATING INFECTION
  申请人：UNIVERSITY OF ROCHESTER

  公开号：US20150238473A1

  公开（公告）日：2015-08-27

  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。