(S)-N-(1-amino-1-oxopropan-2-yl)-4-octylbenzamide | 1198307-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(1-amino-1-oxopropan-2-yl)-4-octylbenzamide
• 英文别名: N-[(2S)-1-amino-1-oxopropan-2-yl]-4-octylbenzamide
• CAS: 1198307-02-6
• 化学式: C₁₈H₂₈N₂O₂
• 分子量: 304.433
• InChiKey: ZOOSPGFVIRUHQR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-正辛基苯甲酸 、 L-丙氨酰胺盐酸盐 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以0.23 mmol的产率得到(S)-N-(1-amino-1-oxopropan-2-yl)-4-octylbenzamide
  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

文献信息

• COMPOSITIONS AND METHODS FOR INHIBITING SPHINGOSINE KINASE
  申请人：Lynch Kevin R.

  公开号：US20110106241A1

  公开（公告）日：2011-05-05

  Amidine analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 & SphK2) are provided. The compounds can prevent angiogenesis in tumor cells.

  提供了可以抑制鞘氨醇激酶1和鞘氨醇激酶2（SphK1和SphK2）活性的酰胺类似物。这些化合物可以防止肿瘤细胞中的血管生成。
• Discovery, Biological Evaluation, and Structure−Activity Relationship of Amidine Based Sphingosine Kinase Inhibitors
  作者：Thomas P. Mathews、Andrew J. Kennedy、Yugesh Kharel、Perry C. Kennedy、Oana Nicoara、Manjula Sunkara、Andrew J. Morris、Brian R. Wamhoff、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1021/jm901860h

  日期：2010.4.8

  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.