2-amino-2-(4-(8-fluorooctyl)phenethyl)propane-1,3-diol | 801289-27-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-2-(4-(8-fluorooctyl)phenethyl)propane-1,3-diol
• 英文别名: 1,3-Propanediol, 2-amino-2-[2-[4-(8-fluorooctyl)phenyl]ethyl]-；2-amino-2-[2-[4-(8-fluorooctyl)phenyl]ethyl]propane-1,3-diol
• CAS: 801289-27-0
• 化学式: C₁₉H₃₂FNO₂
• 分子量: 325.467
• InChiKey: SJOXDBRVMVOJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-2-(4-(8-fluorooctyl)phenethyl)propane-1,3-diol 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.25h， 生成 2-amino-4-[4-(8-fluorooctyl)phenyl]-2-(hydroxymethyl)butyl dihydrogen phosphate
  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 、 全氟丁基磺酰氟 、 caesium carbonate 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 53.0h， 生成 2-amino-2-(4-(8-fluorooctyl)phenethyl)propane-1,3-diol
  参考文献：
  名称：

  [EN] NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
  [FR] NOUVEAUX LIGANDS POUR LE CIBLAGE DE RÉCEPTEURS DE S1P, UTILISÉS DANS L'IMAGERIE IN VIVO ET LE TRAITEMENT DE MALADIES

  摘要：

  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。

  公开号：

  WO2013026765A1

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。
• 2-AMINO-1,3-PROPANEDIOL COMPOUND AND IMMUNOSUPPRESSANT
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0627406A1

  公开（公告）日：1994-12-07

  A 2-amino-1,3-propanediol compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, and an immunosuppressant containing the same as the active ingredient. In said formula R represents optionally substituted linear or branched carbon chain, optionally substituted aryl or optionally substituted cycloalkyl; and R2, R3, R4 and R5, which may be the same or different from one another, represent each hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl. The compound is immunodepressant and useful as an inhibitor against rejection in organ or bone marrow transplantation, as a preventive or remedy for autoimmune diseases and so forth, or a reagent in the medical and pharmaceutical fields.

  一种由通式(I)代表的2-氨基-1,3-丙二醇化合物或其药学上可接受的盐，以及一种以其为活性成分的免疫抑制剂。在所述式中，R 代表任选取代的直链或支链碳链、任选取代的芳基或任选取代的环烷基；而 R2、R3、R4 和 R5（它们彼此可以相同或不同）分别代表氢、烷基、芳烷基、酰基或烷氧基羰基。该化合物具有免疫抑制作用，可作为器官移植或骨髓移植中的排斥抑制剂、自身免疫性疾病的预防或治疗药物等，也可作为医疗和制药领域的试剂。
• USE OF 2-AMINO-1-3-PROPANEDIOL DERIVATIVES FOR THE MANUFACTURE OF A MEDICAMENT FOR THE TREATMENT OF VARIOUS TYPES OF PAIN
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1484057A1

  公开（公告）日：2004-12-08

  The present invention relates to the use of 2-Amino-1,3-propanediol derivatives of the formula I, for the preparation of pharmaceuticals for the prophylaxis or treatment of pain.

  本发明涉及式 I 的 2-氨基-1,3-丙二醇衍生物用于制备预防或治疗疼痛的药物、 用于制备预防或治疗疼痛的药物。
• EP0627406B1
  申请人：——

  公开号：EP0627406B1

  公开（公告）日：1998-10-28