methyl 4-[(2-oxohexadecanoyl)amino]butanoate | 600142-99-2

• 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: methyl 4-[(2-oxohexadecanoyl)amino]butanoate
• 英文别名: Butanoic acid, 4-[(1,2-dioxohexadecyl)amino]-, methyl ester；methyl 4-(2-oxohexadecanoylamino)butanoate
• CAS: 600142-99-2
• 化学式: C₂₁H₃₉NO₄
• 分子量: 369.545
• InChiKey: ZMEMTAXTEWWHOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-[(2-oxohexadecanoyl)amino]butanoate 在 Candida antarctica lipase 、 phosphate buffer 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 72.0h， 以75%的产率得到4-[(2-oxohexadecanoyl)amino]butanoic acid
  参考文献：
  名称：

  酶去除羧基保护基。2.裂解苄基和甲基部分

  摘要：

  酶是用于有效去除甲基和苄基保护基团的通用试剂。来自枯草芽孢杆菌的酯酶（BS2）和来自南极假丝酵母的脂肪酶（CAL-A）可以高产率温和而选择性地除去这些部分，而不会影响其他官能团。

  DOI：

  10.1021/jo051004v
• 作为产物：
  描述：

  4-氨基丁酸甲酯盐酸盐 在 碳酸氢钠 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 sodium hypochlorite 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)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 methyl 4-[(2-oxohexadecanoyl)amino]butanoate
  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

文献信息

• Inhibition of Group IVA Cytosolic Phospholipase A₂ by Novel 2-Oxoamides in Vitro, in Cells, and in Vivo
  作者：George Kokotos、David A. Six、Vassilios Loukas、Timothy Smith、Violetta Constantinou-Kokotou、Dimitra Hadjipavlou-Litina、Stavroula Kotsovolou、Antonia Chiou、Christopher C. Beltzner、Edward A. Dennis

  DOI：10.1021/jm030485c

  日期：2004.7.1

  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.
• Enzymatic Removal of Carboxyl Protecting Groups. 2. Cleavage of the Benzyl and Methyl Moieties
  作者：Efrosini Barbayianni、Irene Fotakopoulou、Marlen Schmidt、Violetta Constantinou-Kokotou、Uwe T. Bornscheuer、George Kokotos

  DOI：10.1021/jo051004v

  日期：2005.10.1

  Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.

  酶是用于有效去除甲基和苄基保护基团的通用试剂。来自枯草芽孢杆菌的酯酶（BS2）和来自南极假丝酵母的脂肪酶（CAL-A）可以高产率温和而选择性地除去这些部分，而不会影响其他官能团。