tert-butyl N-[(R)-2-benzyloxy-1-(tetradecylcarbamoyl)ethyl]carbamate | 243473-99-6

• 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: tert-butyl N-[(R)-2-benzyloxy-1-(tetradecylcarbamoyl)ethyl]carbamate
• 英文别名: tert-butyl N-[(2R)-1-oxo-3-phenylmethoxy-1-(tetradecylamino)propan-2-yl]carbamate
• CAS: 243473-99-6
• 化学式: C₂₉H₅₀N₂O₄
• 分子量: 490.727
• InChiKey: CYIVTRZCIZCLKH-AREMUKBSSA-N

物化性质

• 沸点：
  628.5±55.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  35
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(R)-2-benzyloxy-1-(tetradecylcarbamoyl)ethyl]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以87%的产率得到tert-butyl N-[(2R)-3-hydroxy-1-oxo-1-(tetradecylamino)propan-2-yl]carbamate
  参考文献：
  名称：

  [EN] ORALLY AVAILABLE SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS AND ANTAGONISTS
  [FR] AGONISTES ET ANTAGONISTES DU RECEPTEUR DE LA SPHINGOSINE-1-PHOSPHATE POUVANT ETRE PRIS PAR VOIE ORALE

  摘要：

  公开号：

  WO2005041899A3
• 作为产物：
  描述：

  十四胺 、 N-Boc-O-苄基-D-丝氨酸 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 tert-butyl N-[(R)-2-benzyloxy-1-(tetradecylcarbamoyl)ethyl]carbamate
  参考文献：
  名称：

  Studies on scavenger receptor inhibitors. Part 1: synthesis and structure–activity relationships of novel derivatives of sulfatides

  摘要：

  Scavenger receptors have been proven to be implicated in the formation of atherosclerotic lesions. A series of novel derivatives of sulfatides were synthesized, and their inhibitory activities against incorporation of Dil-acetyl-LDL into macrophages were evaluated in order to clarify the structure-activity relationships of sulfatides as a scavenger receptor inhibitor and find out novel inhibitors with synthetic easiness. The chemical modification of the substructures of sulfatides led to the establishment of the following structure-activity relationships (1) the ceramide moiety can be replaced with another structure bearing two long chains, (2) the galactose moiety can be replaced with another structure or be deleted without a large decrease in the inhibitory activity, (3) the sulfate moiety was crucial, and it was the most preferable functional group for a potent inhibitory activity. The inhibitory activity of (S)-2-octadecanoylamino-2-tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) against incorporation of Dil-acetyl-LDL into macrophages was proven to be based on the inhibition against the binding of acetyl-LDL to the surface of macrophages. We discovered novel scavenger receptor inhibitors with synthetic easiness, such as (S)-2-octadecanoylamino-2-(tetradccylcarbamoyl)ethyl sulfate sodium salt (3a) and 2-octadecanoylamino-1-(octadecanoylaminomethyl)ethyl sulfate sodium salt (13q). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00120-7

文献信息

• Synthesis of para-Alkyl aryl amide analogues of sphingosine-1-phosphate: discovery of potent S1P receptor agonists
  作者：Jeremy J. Clemens、Michael D. Davis、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/s0960-894x(03)00812-6

  日期：2003.10

  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.