(S,2E,4E)-ethyl 6-(tert-butoxycarbonyl)deca-2,4-dienoate | 951035-60-2

• 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,2E,4E)-ethyl 6-(tert-butoxycarbonyl)deca-2,4-dienoate
• CAS: 951035-60-2
• 化学式: C₁₇H₂₉NO₄
• 分子量: 311.422
• InChiKey: XPXBMGXRVXWJFP-INVQJTDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S,2E,4E)-ethyl 6-(tert-butoxycarbonyl)deca-2,4-dienoate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 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 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (S)-6-(2-hydroxypentadecanamido)decanoic acid
  参考文献：
  名称：

  Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.

  DOI：

  10.1021/jm0613673
• 作为产物：
  描述：

  tert-butyl (S)-(1-hydroxyhexan-2-yl)carbamate 在 2,2,6,6-tetramethylpiperidine-1-yloxy free radical lithium hydroxide 、 sodium hypochlorite 、 molecular sieve 、 碳酸氢钠 、 sodium bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 反应 12.0h， 生成 (S,2E,4E)-ethyl 6-(tert-butoxycarbonyl)deca-2,4-dienoate
  参考文献：
  名称：

  Structure−Activity Relationship of 2-Oxoamide Inhibition of Group IVA Cytosolic Phospholipase A₂ and Group V Secreted Phospholipase A₂

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA cPLA(2)) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and GIVA cPLA(2) inhibition. The most potent inhibitors are derived from delta- and gamma-amino acid-based 2-oxoamides. The optimal side-chain moiety is a short nonpolar aliphatic chain. All of the newly developed 2-oxoamides as well as those previously described have now been tested with the human Group V secreted PLA(2) (GV sPLA(2)) and the human Group VIA calcium-independent PLA(2) (GVIA iPLA(2)). Only one 2-oxoamide compound had appreciable inhibition of GV sPLA(2), and none of the potent GIVA cPLA(2) inhibitors inhibited either GV sPLA(2) or GVIA iPLA(2). Two of these specific GIVA cPLA(2) inhibitors were also found to have potent therapeutic effects in animal models of pain and inflammation at dosages well below the control nonsteroidal anti-inflammatory drugs.

  DOI：

  10.1021/jm0613673