3-(2-oxohexadecanamido)propanoic acid | 1268718-07-5

• 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: 3-(2-oxohexadecanamido)propanoic acid
• 英文别名: 3-(2-oxohexadecanoylamino)propanoic acid
• CAS: 1268718-07-5
• 化学式: C₁₉H₃₅NO₄
• 分子量: 341.491
• InChiKey: UWGZWKCCCYBTSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基十六烷酸 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(2-oxohexadecanamido)propanoic acid
  参考文献：
  名称：

  Inhibition of secreted phospholipases A2 by 2-oxoamides based on α-amino acids: Synthesis, in vitro evaluation and molecular docking calculations

  摘要：

  Group IIA secreted phospholipase A(2) (GIIA sPLA(2)) is a member of the mammalian sPLA(2) enzyme family and is associated with various inflammatory conditions. In this study, the synthesis of 2-oxoamides based on alpha-amino acids and the in vitro evaluation against three secreted sPLA(2)s (GIIA, GV and GX) are described. The long chain 2-oxoamide GK126 based on the amino acid (S)-leucine displayed inhibition of human and mouse GIIA sPLA(2)s (IC50 300 nM and 180 nM, respectively). It also inhibited human GV sPLA(2) with similar potency, while it did not inhibit human GX sPLA(2). The elucidation of the stereoelectronic characteristics that affect the in vitro activity of these compounds was achieved by using a combination of simulated annealing to sample low-energy conformations before the docking procedure, and molecular docking calculations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.030

文献信息

• Inhibition of secreted phospholipases A2 by 2-oxoamides based on α-amino acids: Synthesis, in vitro evaluation and molecular docking calculations
  作者：Varnavas D. Mouchlis、Victoria Magrioti、Efrosini Barbayianni、Nathan Cermak、Rob C. Oslund、Thomas M. Mavromoustakos、Michael H. Gelb、George Kokotos

  DOI：10.1016/j.bmc.2010.12.030

  日期：2011.1

  Group IIA secreted phospholipase A(2) (GIIA sPLA(2)) is a member of the mammalian sPLA(2) enzyme family and is associated with various inflammatory conditions. In this study, the synthesis of 2-oxoamides based on alpha-amino acids and the in vitro evaluation against three secreted sPLA(2)s (GIIA, GV and GX) are described. The long chain 2-oxoamide GK126 based on the amino acid (S)-leucine displayed inhibition of human and mouse GIIA sPLA(2)s (IC50 300 nM and 180 nM, respectively). It also inhibited human GV sPLA(2) with similar potency, while it did not inhibit human GX sPLA(2). The elucidation of the stereoelectronic characteristics that affect the in vitro activity of these compounds was achieved by using a combination of simulated annealing to sample low-energy conformations before the docking procedure, and molecular docking calculations. (C) 2011 Elsevier Ltd. All rights reserved.