benzyl (S)-1-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)ethyl-carbamate | 1210045-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl (S)-1-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)ethyl-carbamate
• 英文别名: benzyl N-[(1S)-1-[5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl]ethyl]carbamate
• CAS: 1210045-05-8
• 化学式: C₂₆H₃₃N₃O₃
• 分子量: 435.566
• InChiKey: KHOZVPKKTDCHHV-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (S)-1-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)ethyl-carbamate 在 30% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以0.06 mmol的产率得到(S)-1-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)ethanamine
  参考文献：
  名称：

  Discovery, Biological Evaluation, and Structure−Activity Relationship of Amidine Based Sphingosine Kinase Inhibitors

  摘要：

  Sphingosine 1-phosphate (S1P), a potent phospholipid growth and trophic factor, is synthesized in vivo by two sphingosine kinases. Thus these kinases have been proposed as important drug targets for treatment of hyperproliferative diseases and inflammation. We report here a new class of amidine-based sphingosine analogues that are competitive inhibitors of sphingosine kinases exhibiting varying degrees of enzyme selectivity. These inhibitors display K(I) values in the submicromolar range for both sphingosine kinases and, in cultured vascular smooth muscle cells, decrease S1P levels and initiate growth arrest.

  DOI：

  10.1021/jm901860h
• 作为产物：
  描述：

  benzyl (R,Z)-1-amino-1-(4-octylbenzoyloxyimino)propan-2-ylcarbamate 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以1.14 mmol的产率得到benzyl (S)-1-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)ethyl-carbamate
  参考文献：
  名称：

  Discovery, Biological Evaluation, and Structure−Activity Relationship of Amidine Based Sphingosine Kinase Inhibitors

  摘要：

  Sphingosine 1-phosphate (S1P), a potent phospholipid growth and trophic factor, is synthesized in vivo by two sphingosine kinases. Thus these kinases have been proposed as important drug targets for treatment of hyperproliferative diseases and inflammation. We report here a new class of amidine-based sphingosine analogues that are competitive inhibitors of sphingosine kinases exhibiting varying degrees of enzyme selectivity. These inhibitors display K(I) values in the submicromolar range for both sphingosine kinases and, in cultured vascular smooth muscle cells, decrease S1P levels and initiate growth arrest.

  DOI：

  10.1021/jm901860h