(S)-ethyl 2-(2-(2-oxohexadecanamido)hexyloxy)acetate | 926033-94-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-ethyl 2-(2-(2-oxohexadecanamido)hexyloxy)acetate
• 英文别名: ethyl 2-[(2S)-2-(2-oxohexadecanoylamino)hexoxy]acetate
• CAS: 926033-94-5
• 化学式: C₂₆H₄₉NO₅
• 分子量: 455.679
• InChiKey: UKJMDBBPPAHJAV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-((2S)-2-(2-hydroxyhexadecanamido)hexyloxy)acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到(S)-ethyl 2-(2-(2-oxohexadecanamido)hexyloxy)acetate
  参考文献：
  名称：

  2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides

  摘要：

  A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities towards two human intracellular phospholipases A(2) (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase A(2) (GV sPLA(2)) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA(2) inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA2. The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA(2) inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC50 value of 2 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.069

文献信息

• 2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides
  作者：Efrosini Barbayianni、Daren Stephens、Andrej Grkovich、Victoria Magrioti、Yuan-Hao Hsu、Panagiotis Dolatzas、Dimitrios Kalogiannidis、Edward A. Dennis、George Kokotos

  DOI：10.1016/j.bmc.2009.03.069

  日期：2009.7

  A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities towards two human intracellular phospholipases A(2) (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase A(2) (GV sPLA(2)) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA(2) inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA2. The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA(2) inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC50 value of 2 mu M. (C) 2009 Elsevier Ltd. All rights reserved.