4-(2-hydroxy-nonadec-10-enoylamino)butyric acid methyl ester

• 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: 4-(2-hydroxy-nonadec-10-enoylamino)butyric acid methyl ester
• 英文别名: methyl 4-[[(Z)-2-hydroxynonadec-10-enoyl]amino]butanoate
• 化学式: C₂₄H₄₅NO₄
• 分子量: 411.626
• InChiKey: OSSWXOMRIMSTJJ-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-nonadec-10-enoylamino)butyric acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Differential Inhibition of Group IVA and Group VIA Phospholipases A₂ by 2-Oxoamides

  摘要：

  Inhibitors of the Group IVA phospholipase A(2) (GIVA cPLA(2)) and GVIA iPLA(2) are useful tools for defining the roles of these enzymes in cellular signaling and inflammation. We have developed inhibitors of GVIA iPLA(2) building upon the 2-oxoamide backbone that are uncharged, containing ester groups. Although the most potent inhibitors of GVIA iPLA(2) also inhibited GIVA cPLA(2), there were three 2-oxoamide compounds that selectively and weakly inhibited GVIA iPLA(2). We further show that several potent 2-oxoamide inhibitors of GIVA cPLA(2) containing free carboxylic groups (Kokotos et al. J. Med. Chem. 2002, 45, 2891-2893) do not inhibit GVIA iPLA(2) and are, therefore, selective GIVA cPLA(2) inhibitors.

  DOI：

  10.1021/jm050993h
• 作为产物：
  描述：

  4-氨基丁酸甲酯盐酸盐 、 2-hydroxy-10(Z)-nonadecenoic acid 在 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 二氯甲烷 为溶剂， 以82%的产率得到4-(2-hydroxy-nonadec-10-enoylamino)butyric acid methyl ester
  参考文献：
  名称：

  Differential Inhibition of Group IVA and Group VIA Phospholipases A₂ by 2-Oxoamides

  摘要：

  Inhibitors of the Group IVA phospholipase A(2) (GIVA cPLA(2)) and GVIA iPLA(2) are useful tools for defining the roles of these enzymes in cellular signaling and inflammation. We have developed inhibitors of GVIA iPLA(2) building upon the 2-oxoamide backbone that are uncharged, containing ester groups. Although the most potent inhibitors of GVIA iPLA(2) also inhibited GIVA cPLA(2), there were three 2-oxoamide compounds that selectively and weakly inhibited GVIA iPLA(2). We further show that several potent 2-oxoamide inhibitors of GIVA cPLA(2) containing free carboxylic groups (Kokotos et al. J. Med. Chem. 2002, 45, 2891-2893) do not inhibit GVIA iPLA(2) and are, therefore, selective GIVA cPLA(2) inhibitors.

  DOI：

  10.1021/jm050993h

文献信息

• Differential Inhibition of Group IVA and Group VIA Phospholipases A₂ by 2-Oxoamides
  作者：Daren Stephens、Efrosini Barbayianni、Violetta Constantinou-Kokotou、Anna Peristeraki、David A. Six、Jennifer Cooper、Richard Harkewicz、Raymond A. Deems、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm050993h

  日期：2006.5.1

  Inhibitors of the Group IVA phospholipase A(2) (GIVA cPLA(2)) and GVIA iPLA(2) are useful tools for defining the roles of these enzymes in cellular signaling and inflammation. We have developed inhibitors of GVIA iPLA(2) building upon the 2-oxoamide backbone that are uncharged, containing ester groups. Although the most potent inhibitors of GVIA iPLA(2) also inhibited GIVA cPLA(2), there were three 2-oxoamide compounds that selectively and weakly inhibited GVIA iPLA(2). We further show that several potent 2-oxoamide inhibitors of GIVA cPLA(2) containing free carboxylic groups (Kokotos et al. J. Med. Chem. 2002, 45, 2891-2893) do not inhibit GVIA iPLA(2) and are, therefore, selective GIVA cPLA(2) inhibitors.