N-{4-[4-(8-fluorooctyl)phenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl}acetamide | 1426083-88-6

• 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: N-{4-[4-(8-fluorooctyl)phenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl}acetamide
• 英文别名: N-[4-[4-(8-fluorooctyl)phenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl]acetamide
• CAS: 1426083-88-6
• 化学式: C₂₁H₃₄FNO₃
• 分子量: 367.504
• InChiKey: ASBRJIOJQRTPHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-{4-[4-(8-fluorooctyl)phenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl}acetamide 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 {4-[4-(8-fluorooctyl)phenethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}methanol
  参考文献：
  名称：

  Synthesis and Evaluation of Fluorinated Fingolimod (FTY720) Analogues for Sphingosine-1-Phosphate Receptor Molecular Imaging by Positron Emission Tomography

  摘要：

  Sphingosine-1-phosphate (S1P) is a lysophospholipid that evokes a variety of biological responses via stimulation of a set of cognate G-protein coupled receptors (GPCRs): S1P(1)-S1P(5). S1P and its receptors (S1PRs) play important roles in the immune, cardiovascular, and central nervous systems and have also been implicated in carcinogenesis. Recently, the S1P analogue Fingolimod (FTY720) has been approved for the treatment of patients with relapsing multiple sclerosis. This work presents the synthesis of various fluorinated structural analogues of FTY720, their in vitro and in vivo biological testing, and their development and application as [F-18]radiotracers for the study of S1PR biodistribution and imaging in mice using small-animal positron emission tomography (PET).

  DOI：

  10.1021/jm502021d
• 作为产物：
  描述：

  2-bromo-1-[4-(8-hydroxyoctyl)phenyl]ethanone 在 三乙基硅烷 、 锂硼氢 、 乙醇 、 全氟丁基磺酰氟 、 caesium carbonate 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 52.0h， 生成 N-{4-[4-(8-fluorooctyl)phenyl]-1-hydroxy-2-(hydroxymethyl)butan-2-yl}acetamide
  参考文献：
  名称：

  Synthesis and Evaluation of Fluorinated Fingolimod (FTY720) Analogues for Sphingosine-1-Phosphate Receptor Molecular Imaging by Positron Emission Tomography

  摘要：

  Sphingosine-1-phosphate (S1P) is a lysophospholipid that evokes a variety of biological responses via stimulation of a set of cognate G-protein coupled receptors (GPCRs): S1P(1)-S1P(5). S1P and its receptors (S1PRs) play important roles in the immune, cardiovascular, and central nervous systems and have also been implicated in carcinogenesis. Recently, the S1P analogue Fingolimod (FTY720) has been approved for the treatment of patients with relapsing multiple sclerosis. This work presents the synthesis of various fluorinated structural analogues of FTY720, their in vitro and in vivo biological testing, and their development and application as [F-18]radiotracers for the study of S1PR biodistribution and imaging in mice using small-animal positron emission tomography (PET).

  DOI：

  10.1021/jm502021d

文献信息

• [EN] NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES<br/>[FR] NOUVEAUX LIGANDS POUR LE CIBLAGE DE RÉCEPTEURS DE S1P, UTILISÉS DANS L'IMAGERIE IN VIVO ET LE TRAITEMENT DE MALADIES
  申请人：UNIV MUENSTER WILHELMS

  公开号：WO2013026765A1

  公开（公告）日：2013-02-28

  The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

  本发明涉及具有以下式（I）和（II）的新化合物，其在与S1P受体相关的疾病或紊乱的预防、治疗和体内诊断方面具有用途，特别是在与神经酰胺-1-磷酸鞘氨醇（S1P）及其类似物的调节功能相关的疾病中，如炎症、疼痛、自身免疫疾病和心血管疾病。
• NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
  申请人：Haufe Guenter

  公开号：US20140170067A1

  公开（公告）日：2014-06-19

  The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

  本发明涉及具有以下化学式(I)和(II)的新化合物，其在预防、治疗和诊断与S1P受体相关的疾病或疾病的体内诊断中有用，特别是在与鞘氨醇-1-磷酸酯（S1P）及其类似物的调节功能相关的疾病中，如炎症、疼痛、自身免疫疾病和心血管疾病。
• US9345791B2
  申请人：——

  公开号：US9345791B2

  公开（公告）日：2016-05-24
• Synthesis and Evaluation of Fluorinated Fingolimod (FTY720) Analogues for Sphingosine-1-Phosphate Receptor Molecular Imaging by Positron Emission Tomography
  作者：Rizwan S. Shaikh、Stefanie S. Schilson、Stefan Wagner、Sven Hermann、Petra Keul、Bodo Levkau、Michael Schäfers、Günter Haufe

  DOI：10.1021/jm502021d

  日期：2015.4.23

  Sphingosine-1-phosphate (S1P) is a lysophospholipid that evokes a variety of biological responses via stimulation of a set of cognate G-protein coupled receptors (GPCRs): S1P(1)-S1P(5). S1P and its receptors (S1PRs) play important roles in the immune, cardiovascular, and central nervous systems and have also been implicated in carcinogenesis. Recently, the S1P analogue Fingolimod (FTY720) has been approved for the treatment of patients with relapsing multiple sclerosis. This work presents the synthesis of various fluorinated structural analogues of FTY720, their in vitro and in vivo biological testing, and their development and application as [F-18]radiotracers for the study of S1PR biodistribution and imaging in mice using small-animal positron emission tomography (PET).