ethyl 2-((2S)-2-(2-hydroxyhexadecanamido)hexyloxy)acetate | 1178909-90-4

• 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: ethyl 2-((2S)-2-(2-hydroxyhexadecanamido)hexyloxy)acetate
• 英文别名: ethyl 2-[(2S)-2-(2-hydroxyhexadecanoylamino)hexoxy]acetate
• CAS: 1178909-90-4
• 化学式: C₂₆H₅₁NO₅
• 分子量: 457.695
• InChiKey: RENFCVRWZCDGRR-UXMRNZNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-羟基十六烷酸 、 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， 生成 ethyl 2-((2S)-2-(2-hydroxyhexadecanamido)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-OXAMIDE INHIBITORS OF PHOSPHOLIPASE A2 ACTIVITY AND CELLULAR ARACHIDONATE RELEASE BASED ON DIPEPTIDES AND PSEUDOPEPTIDES
  申请人：Dennis Edward A.

  公开号：US20120095096A1

  公开（公告）日：2012-04-19

  The disclosure provides a series of 2-oxoamides based on dipeptides and pseudodipeptides, which were synthesized and their activities toward two human intracellular phospholipases A2 (GIVA CPLA 2 and GVIA 1PLA 2 ) and one human secretory phospholipase A2 (GVsPLA 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 iPLA 2 . The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied. It was found that selective GIVA cPLA 2 inhibitors preferentially inhibited cellular arachidonic acid release; in which one pseudodipeptide gave an IC50 value of 2 μM.

  该披露提供了一系列基于二肽和假二肽的2-氧代酰胺，这些化合物已被合成，并评估了它们对两种人类细胞内磷脂酶A2（GIVA CPLA2和GVIA 1PLA2）以及一种人类分泌型磷脂酶A2（GVsPLA2）的活性。含有自由羧基的衍生物是选择性的GIVA cPLA2抑制剂。一种基于乙酰化假二肽的2-氧代酰胺是首个优先抑制GVIA iPLA2的化合物。还研究了2-氧代酰胺对RAW 264.7巨噬细胞中花生四烯酸生成的影响。发现选择性的GIVA cPLA2抑制剂优先抑制细胞花生四烯酸释放；其中一个假二肽给出了2μM的IC50值。
• US8580852B2
  申请人：——

  公开号：US8580852B2

  公开（公告）日：2013-11-12
• [EN] 2-OXAMIDE INHIBITORS OF PHOSPHOLIPASE A2 ACTIVITY AND CELLULAR ARACHIDONATE RELEASE BASED ON DIPEPTIDES AND PSEUDOPEPTIDES<br/>[FR] INHIBITEURS 2-OXAMIDE D'ACTIVITÉ PHOSPHOLIPASE A2 ET DE LIBÉRATION CELLULAIRE D'ARACHIDONATE FONDÉS SUR DIPEPTIDES ET PSEUDOPEPTIDES
  申请人：UNIV CALIFORNIA

  公开号：WO2010123832A2

  公开（公告）日：2010-10-28

  The disclosure provides a series of 2-oxoamides based on dipeptides and pseudodipeptides, which were synthesized and their activities toward two human intracellular phospholipases A2 (GIVA CPLA2 and GVIA 1PLA2) and one human secretory phospholipase A2 (GV sPLA2) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA2 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. It was found that selective GIVA cPLA2 inhibitors preferentially inhibited cellular arachidonic acid release; in which one pseudodipeptide gave an IC50 value of 2 μM.
• 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.