[(1R,2S)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester | 868553-65-5

• 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: [(1R,2S)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R,3S)-3-hydroxy-1-(4-octylanilino)-1-oxobutan-2-yl]carbamate
• CAS: 868553-65-5
• 化学式: C₂₃H₃₈N₂O₄
• 分子量: 406.566
• InChiKey: TWKKTTJXYBPSKX-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 在 四氮唑 、 三甲基溴硅烷 、 sulfur 、 苯硫酚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 Thiophosphoric acid O-[(1S,2R)-2-amino-1-methyl-2-(4-octyl-phenylcarbamoyl)-ethyl] ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057
• 作为产物：
  描述：

  [(1R,2S)-2-Benzyloxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以96%的产率得到[(1R,2S)-2-Hydroxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057

文献信息

• 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.