4-(2-oxo-6-phenyl-hexanoylamino)-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-oxo-6-phenyl-hexanoylamino)-butyric acid methyl ester
• 英文别名: Methyl 4-[(2-oxo-6-phenylhexanoyl)amino]butanoate
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: AHFFTJMTYRBOMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基丁酸甲酯盐酸盐 在 碳酸氢钠 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 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 、 sodium bromide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 1.25h， 生成 4-(2-oxo-6-phenyl-hexanoylamino)-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

• Systemic and Intrathecal Effects of a Novel Series of Phospholipase A2 Inhibitors on Hyperalgesia and Spinal Pge2 Release
  申请人：Dennis Edward

  公开号：US20080319065A1

  公开（公告）日：2008-12-25

  Phospholipase A 2 (PLA 2 ) forins are expressed in spinal cord whose inhibition induces a potent antihyperalgesia. PLA 2 inhibitor compounds are provided that include a common motif consisting of a 2-oxoamide with a hydrocarbon tail and a four carbon tether. The compounds block Group IVA calcium dependent PLA 2 (cPLA 2 ) and/or Group VIA calcium independent PLA 2 (iPLA 2 ) and/or Group V secreted PLA 2 (sPLA 2 ).

  磷脂酶A2（PLA2）家族在脊髓中表达，其抑制可引起强有效的抗痛觉过敏。提供了PLA2抑制剂化合物，包括一个共同的基序，由一个带有碳氢尾和四个碳链的2-氧酰胺组成。这些化合物可以阻止IV A组钙依赖性PLA2（cPLA2）和/或VI A组钙非依赖性PLA2（iPLA2）和/或V组分泌型PLA2（sPLA2）。
• SYSTEMIC AND INTRATHECAL EFFECTS OF A NOVEL SERIES OF PHOSPHOLIPASE A2 INHIBITORS ON HYPERALGESIA AND SPINAL PGE2 RELEASE
  申请人：The Regents of the University of California

  公开号：EP1937247A2

  公开（公告）日：2008-07-02
• US7745489B2
  申请人：——

  公开号：US7745489B2

  公开（公告）日：2010-06-29
• [EN] SYSTEMIC AND INTRATHECAL EFFECTS OF A NOVEL SERIES OF PHOSPHOLIPASE A2 INHIBITORS ON HYPERALGESIA AND SPINAL PGE2 RELEASE<br/>[FR] EFFETS SYSTÉMIQUES ET INTRATHÉCAUX D'UNE NOUVELLE GAMME D'INHIBITEURS DE PHOSPHOLIPASE A2 SUR L'HYPERALGÉSIE ET LA LIBÉRATION SPINALE DE PGE2
  申请人：UNIV CALIFORNIA

  公开号：WO2007022443A2

  公开（公告）日：2007-02-22

  [EN] Phospholipase A₂ (PLA₂) forins are expressed in spinal cord whose inhibition induces a potent antihyperalgesia. PLA₂ inhibitor compounds are provided that include a common motif consisting of a 2-oxoamide with a hydrocarbon tail and a four carbon tether. The compounds block Group IVA calcium dependent PLA₂ (cPLA₂) and/or Group VIA calcium independent PLA₂ (iPLA₂) and/or Group V secreted PLA₂ (sPLA₂).
  [FR] L'expression des forines de type phospholipase A₂ (PLA₂) dans la moelle épinière induit une puissante anti-hyperalgésie. La présente invention décrit des composés inhibiteurs de PLA₂ qui incluent un motif commun constitué d'un 2-oxoamide doté d'une queue hydrocarbure et d'une attache constituée de quatre carbones. Les composés bloquent la PLA₂ calcium-dépendante du Groupe IVA (cPLA₂) et/ou la PLA₂ calcium-indépendante du Groupe VIA (iPLA₂) et/ou la PLA₂ sécrétée du Groupe V (sPLA₂).
• 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.