[(R)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester | 448959-72-6

• 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: [(R)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl (R)-(3-hydroxy-1-((4-octylphenyl)amino)-1-oxopropan-2-yl)carbamate
• CAS: 448959-72-6
• 化学式: C₂₂H₃₆N₂O₄
• 分子量: 392.539
• InChiKey: YDVHODZRYZEEOP-LJQANCHMSA-N

物化性质

• 沸点：
  580.6±50.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(R)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 在 四氮唑 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 VPC22173
  参考文献：
  名称：

  Synthesis of para-Alkyl aryl amide analogues of sphingosine-1-phosphate: discovery of potent S1P receptor agonists

  摘要：

  Sphingosine-1-phosphate (S1P) is a biologically active lysophospholipid with the capacity to induce a broad range of cellular responses via its interaction with the S1P family of G-protein coupled receptors. This report describes the synthesis of several potent S1P receptor agonists. For instance, compound 9c displayed an EC50=8.6 nM at the S1P(1) receptor using a [gamma-S-35]GTP binding assay as compared to an EC50=4.5 nM for the endogenous ligand. We also report the effects associated with introduction of a phenyl ring between the 'linker' and 'lipophilic tail' regions of the analogues, for example total loss of activity at S1P(2) and increased agonism at S1P(5). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00812-6
• 作为产物：
  描述：

  4-辛基苯胺 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 生成 [(R)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  [EN] NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS
  [FR] NOUVEAUX ANTAGONISTES SELECTIFS DU RECEPTEUR DE L'ACIDE LYSOPHOSPHATIDIQUE

  摘要：

  公开号：

  WO2005115150A3

文献信息

• Synthesis of FTY720 (Fingolimod) Derivatives Containing Serine Structure
  作者：Yoon Sin Oh、Taeho Lee、Sang Mi Shin、Jitendra Shrestha、Doohyun Lee、Eun-Young Park、Dong Jae Baek

  DOI：10.1002/bkcs.11370

  日期：2018.2
• Discovery of novel sphingosine kinase 1 inhibitors
  作者：Yibin Xiang、Gary Asmussen、Michael Booker、Bradford Hirth、John L. Kane、Junkai Liao、Kevin D. Noson、Christopher Yee

  DOI：10.1016/j.bmcl.2009.09.022

  日期：2009.11

  Sphingosine kinase 1 (SK1) is an important enzyme that regulates the balance between ceramide and sphingosine-1-phosphate (S1P). Potent and novel SK1 inhibitors (6ag, 9ab and 12aa) have been discovered through a series of modi. cations of sphingosine ( 1), the substrate of this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.