(4R)-5-(ethylcarbamoyloxy)-4-(2-hydroxydodecanamido)pentanoic acid | 951035-78-2

• 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: (4R)-5-(ethylcarbamoyloxy)-4-(2-hydroxydodecanamido)pentanoic acid
• CAS: 951035-78-2
• 化学式: C₂₀H₃₈N₂O₆
• 分子量: 402.532
• InChiKey: ARMVEKDNRXIJSE-TZHYSIJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  28.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  124.96
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R)-5-(ethylcarbamoyloxy)-4-(2-hydroxydodecanamido)pentanoic acid 在 2,2,6,6-tetramethylpiperidine-1-yloxy free radical sodium hypochlorite 、 碳酸氢钠 、 sodium bromide 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 以56%的产率得到(4R)-5-(ethylcarbamoyloxy)-4-(2-oxododecanoylamino)pentanoic acid
  参考文献：
  名称：

  Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.

  DOI：

  10.1021/jm0613673
• 作为产物：
  描述：

  methyl 4-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 12.0h， 生成 (4R)-5-(ethylcarbamoyloxy)-4-(2-hydroxydodecanamido)pentanoic acid
  参考文献：
  名称：

  Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.

  DOI：

  10.1021/jm0613673