benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate | 600143-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate
• 英文别名: Benzyl(E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate；benzyl (E,4S)-4-(2-hydroxydodecanoylamino)oct-2-enoate
• CAS: 600143-18-8
• 化学式: C₂₇H₄₃NO₄
• 分子量: 445.643
• InChiKey: YPGSWEXXRLJOTI-ZSXATBJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (S)-4-(2-Hydroxy-dodecanoylamino)-octanoic acid
  参考文献：
  名称：

  Inhibition of Group IVA Cytosolic Phospholipase A₂ by Novel 2-Oxoamides in Vitro, in Cells, and in Vivo

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA PLA(2)) is a particularly attractive target for drug development because it is the rate-limiting provider of proinflammatory mediators. We previously reported the discovery of novel 2-oxoamides that inhibit GIVA PLA(2) [Kokotos, G.; et al. J. Med. Chem. 2002, 45, 2891-2893]. In the present work, we have further explored this class of inhibitors and found that the 2-oxoamide functionality is more potent when it contains a long 2-oxoacyl residue and a free carboxy group. Long-chain 2-oxoamides based on gamma-aminobutyric acid and gamma-norleucine are potent inhibitors of GIVA PLA(2). Such inhibitors act through a fast and reversible mode of inhibition in vitro, are able to block the production of arachidonic acid and prostaglandin E-2 in cells, and demonstrate potent in vivo antiinflammatory and analgesic activity.

  DOI：

  10.1021/jm030485c
• 作为产物：
  描述：

  氨甲酸,[(1S)-1-甲酰基戊基]-,1,1-二甲基乙基酯 在 盐酸 、 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 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate
  参考文献：
  名称：

  Novel 2-Oxoamide Inhibitors of Human Group IVA Phospholipase A₂

  摘要：

  A novel class of potent human cytosolic phospholipase A(2) (GIVA PLA(2)) inhibitors was developed. These inhibitors were designed to contain the 2-oxoamide functionality and a free carboxyl group. Among the compounds tested, a long-chain 2-oxoamide containing L-gamma-norleucine was the most potent inhibitor, causing a 50% decrease in GIVA PLA2 activity at 0.009 mole fraction.

  DOI：

  10.1021/jm025538p

文献信息

• Compositions and methods for inhibition of phospholipase a2 mediated inflammation
  申请人：Dennis Edward

  公开号：US20050148549A1

  公开（公告）日：2005-07-07

  Specific, highly potent 2-oxo-amide based inhibitors of phospholipase A 2 (PLA 2 ) activity are provided. A role for PLA 2 activity in spinally mediated inflammatory processes is established, and a method for treating hyperalgesia and other inflammatory conditions associated with PLA 2 activity is provided.

  提供了基于2-氧代酰胺的特异性、高效的磷脂酶A2（PLA2）活性抑制剂。已经确定了PLA2活性在脊髓介导的炎症过程中的作用，并提供了一种用于治疗与PLA2活性相关的高痛感和其他炎症病症的方法。
• Compositions and methods for inhibition of phospholipase A2 mediated inflammation
  申请人：The Regents of the University of California

  公开号：US07745489B2

  公开（公告）日：2010-06-29

  Specific, highly potent 2-oxo-amide based inhibitors of phospholipase A2 (PLA2) activity are provided. A role for PLA2 activity in spinally mediated inflammatory processes is established, and a method for treating hyperalgesia and other inflammatory conditions associated with PLA2 activity is provided.

  提供了基于2-氧代酰胺的特异性、高效的磷脂酶A2（PLA2）抑制剂。建立了PLA2活性在脊髓介导的炎症过程中的作用，并提供了一种治疗与PLA2活性相关的高痛和其他炎症病症的方法。
• US7745489B2
  申请人：——

  公开号：US7745489B2

  公开（公告）日：2010-06-29