1-(4-octylbenzyl)piperidin-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-octylbenzyl)piperidin-4-ol
• 英文别名: 1-[(4-Octylphenyl)methyl]piperidin-4-ol；1-[(4-octylphenyl)methyl]piperidin-4-ol
• 化学式: C₂₀H₃₃NO
• 分子量: 303.488
• InChiKey: DXWCHZAGBSYJBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘苄醇 在 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 生成 1-(4-octylbenzyl)piperidin-4-ol
  参考文献：
  名称：

  [EN] SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE
  [FR] INHIBITEURS SÉLECTIFS ET ACTIVATEURS ALLOSTÉRIQUES DE LA SPHINGOSINE KINASE

  摘要：

  公开号：

  WO2014118556A3

文献信息

• [EN] SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS ET ACTIVATEURS ALLOSTÉRIQUES DE LA SPHINGOSINE KINASE
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2014118556A3

  公开（公告）日：2014-09-25
• Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors
  作者：Dong Jae Baek、Neil MacRitchie、Nahoum G. Anthony、Simon P. Mackay、Susan Pyne、Nigel J. Pyne、Robert Bittman

  DOI：10.1021/jm401399c

  日期：2013.11.27

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.