(4R)-methyl 4-(2-hydroxyhexadecanamido)-6-methylheptanoate | 1100655-49-9

• 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: (4R)-methyl 4-(2-hydroxyhexadecanamido)-6-methylheptanoate
• 英文别名: methyl (4R)-4-(2-hydroxyhexadecanoylamino)-6-methylheptanoate
• CAS: 1100655-49-9
• 化学式: C₂₅H₄₉NO₄
• 分子量: 427.668
• InChiKey: KMJCLECRTCUHLU-WTQRLHSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (4R)-methyl 4-(2-hydroxyhexadecanamido)-6-methylheptanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到(R)-methyl 6-methyl-4-(2-oxohexadecanamido)heptanoate
  参考文献：
  名称：

  Structure–activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes

  摘要：

  A variety of 2-oxoamides and related amides based on natural and non-natural amino acids were synthesized. Their activity on two human intracellular phospholipases (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase (GV sPLA(2)) was evaluated. We show that an amide based on (R)-gamma-norleucine is a highly selective inhibitor of GV sPLA2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.046
• 作为产物：
  描述：

  2-羟基十六烷酸 、 (4S)-4-[(tert-butyloxycarbonyl)amino]-6-methylhept-2-enoic acid methyl ester 在 10% Pd/C 、 氢气 、 盐酸 、 水 、 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 作用下， 以 乙醇 、 乙醚 、 二氯甲烷 为溶剂， 以57%的产率得到(4R)-methyl 4-(2-hydroxyhexadecanamido)-6-methylheptanoate
  参考文献：
  名称：

  Structure–activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes

  摘要：

  A variety of 2-oxoamides and related amides based on natural and non-natural amino acids were synthesized. Their activity on two human intracellular phospholipases (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase (GV sPLA(2)) was evaluated. We show that an amide based on (R)-gamma-norleucine is a highly selective inhibitor of GV sPLA2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.046

文献信息

• Phospholipase A2 Inhibitors and their Use in Treating Neurological Injury and Disease
  申请人：Dennis Edward A.

  公开号：US20110105610A1

  公开（公告）日：2011-05-05

  Phospholipase A 2 (PLA 2 ) forms 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 ). Pharmaceutical compositions of compounds having cPLA 2 inhibitory activity (but not iPLA 2 or sPLA 2 inhibitory activity) are useful in treating multiple sclerosis, while compositions of compounds having sPLA 2 inhibitory activity (as well as iPLA 2 and CPLA 2 activity) are useful in treating spinal cord injuries (with related functional recovery).
• US8420852B2
  申请人：——

  公开号：US8420852B2

  公开（公告）日：2013-04-16
• Structure–activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes
  作者：Georgia Antonopoulou、Efrosini Barbayianni、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1016/j.bmc.2008.10.046

  日期：2008.12.15

  A variety of 2-oxoamides and related amides based on natural and non-natural amino acids were synthesized. Their activity on two human intracellular phospholipases (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase (GV sPLA(2)) was evaluated. We show that an amide based on (R)-gamma-norleucine is a highly selective inhibitor of GV sPLA2. (C) 2008 Elsevier Ltd. All rights reserved.