N-[(S)-2-(4-benzyloxy)phenyl-1-(tetradecylcarbamoyl)ethyl]octadecanamide | 243474-20-6

• 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: N-[(S)-2-(4-benzyloxy)phenyl-1-(tetradecylcarbamoyl)ethyl]octadecanamide
• 英文别名: O-benzyl-N-octadecanoyl-L-tyrosinamide；N-[(2S)-1-oxo-3-(4-phenylmethoxyphenyl)-1-(tetradecylamino)propan-2-yl]octadecanamide
• CAS: 243474-20-6
• 化学式: C₄₈H₈₀N₂O₃
• 分子量: 733.175
• InChiKey: UXUDNAQULPNSEJ-DXQCBLCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  53
• 可旋转键数：
  36
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(S)-2-(4-benzyloxy)phenyl-1-(tetradecylcarbamoyl)ethyl]octadecanamide 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 46.0h， 生成 N-[(R)-2-(4-hydroxyphenyl)-1-(tetradecylcarbamoyl)ethyl]octadecanamide
  参考文献：
  名称：

  Studies on scavenger receptor inhibitors. Part 1: synthesis and structure–activity relationships of novel derivatives of sulfatides

  摘要：

  Scavenger receptors have been proven to be implicated in the formation of atherosclerotic lesions. A series of novel derivatives of sulfatides were synthesized, and their inhibitory activities against incorporation of Dil-acetyl-LDL into macrophages were evaluated in order to clarify the structure-activity relationships of sulfatides as a scavenger receptor inhibitor and find out novel inhibitors with synthetic easiness. The chemical modification of the substructures of sulfatides led to the establishment of the following structure-activity relationships (1) the ceramide moiety can be replaced with another structure bearing two long chains, (2) the galactose moiety can be replaced with another structure or be deleted without a large decrease in the inhibitory activity, (3) the sulfate moiety was crucial, and it was the most preferable functional group for a potent inhibitory activity. The inhibitory activity of (S)-2-octadecanoylamino-2-tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) against incorporation of Dil-acetyl-LDL into macrophages was proven to be based on the inhibition against the binding of acetyl-LDL to the surface of macrophages. We discovered novel scavenger receptor inhibitors with synthetic easiness, such as (S)-2-octadecanoylamino-2-(tetradccylcarbamoyl)ethyl sulfate sodium salt (3a) and 2-octadecanoylamino-1-(octadecanoylaminomethyl)ethyl sulfate sodium salt (13q). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00120-7
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 N-[(S)-2-(4-benzyloxy)phenyl-1-(tetradecylcarbamoyl)ethyl]octadecanamide
  参考文献：
  名称：

  Studies on scavenger receptor inhibitors. Part 1: synthesis and structure–activity relationships of novel derivatives of sulfatides

  摘要：

  Scavenger receptors have been proven to be implicated in the formation of atherosclerotic lesions. A series of novel derivatives of sulfatides were synthesized, and their inhibitory activities against incorporation of Dil-acetyl-LDL into macrophages were evaluated in order to clarify the structure-activity relationships of sulfatides as a scavenger receptor inhibitor and find out novel inhibitors with synthetic easiness. The chemical modification of the substructures of sulfatides led to the establishment of the following structure-activity relationships (1) the ceramide moiety can be replaced with another structure bearing two long chains, (2) the galactose moiety can be replaced with another structure or be deleted without a large decrease in the inhibitory activity, (3) the sulfate moiety was crucial, and it was the most preferable functional group for a potent inhibitory activity. The inhibitory activity of (S)-2-octadecanoylamino-2-tetradecylcarbamoyl)ethyl sulfate sodium salt (3a) against incorporation of Dil-acetyl-LDL into macrophages was proven to be based on the inhibition against the binding of acetyl-LDL to the surface of macrophages. We discovered novel scavenger receptor inhibitors with synthetic easiness, such as (S)-2-octadecanoylamino-2-(tetradccylcarbamoyl)ethyl sulfate sodium salt (3a) and 2-octadecanoylamino-1-(octadecanoylaminomethyl)ethyl sulfate sodium salt (13q). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00120-7