(Z)-N-(4-fluoro-1-hydroxy-2-(hydroxymethyl)octadec-4-en-2-yl)acetamide | 1426083-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-N-(4-fluoro-1-hydroxy-2-(hydroxymethyl)octadec-4-en-2-yl)acetamide
• 英文别名: N-[(Z)-4-fluoro-1-hydroxy-2-(hydroxymethyl)octadec-4-en-2-yl]acetamide
• CAS: 1426083-71-7
• 化学式: C₂₁H₄₀FNO₃
• 分子量: 373.552
• InChiKey: CXVXWEZAYNBLEK-HKWRFOASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (Z)-N-(4-fluoro-1-hydroxy-2-(hydroxymethyl)octadec-4-en-2-yl)acetamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以87%的产率得到(Z)-2-amino-2-(2-fluorohexadec-2-en-1-yl)propane-1,3-diol
  参考文献：
  名称：

  NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

  摘要：

  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。

  公开号：

  US20140170067A1
• 作为产物：
  描述：

  (Z)-diethyl-2-acetamido-2-(2-fluorohexadec-2-ene-1-yl)malonate 在 sodium borohydrid 、 乙醇 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 144.0h， 以51%的产率得到(Z)-N-(4-fluoro-1-hydroxy-2-(hydroxymethyl)octadec-4-en-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of new ligands for targeting the S1P1 receptor

  摘要：

  Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P(1-5)). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P(1) receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [F-18]-labelling. The radioligands shall enable the imaging of S1P(1) receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.014

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 of new ligands for targeting the S1P1 receptor
  作者：Stefanie S. Schilson、Petra Keul、Rizwan S. Shaikh、Michael Schäfers、Bodo Levkau、Günter Haufe

  DOI：10.1016/j.bmc.2015.01.014

  日期：2015.3

  Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P(1-5)). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P(1) receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [F-18]-labelling. The radioligands shall enable the imaging of S1P(1) receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases. (C) 2015 Elsevier Ltd. All rights reserved.