N-[(S)-1-tetradecylcarbamoyl-2-(3-sulfo-β-D-galactopyranosyl)oxyethyl]hexadecanamide

• 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: N-[(S)-1-tetradecylcarbamoyl-2-(3-sulfo-β-D-galactopyranosyl)oxyethyl]hexadecanamide
• 英文别名: [(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2S)-2-(octadecanoylamino)-3-oxo-3-(tetradecylamino)propoxy]oxan-4-yl] hydrogen sulfate
• 化学式: C₄₁H₈₀N₂O₁₁S
• 分子量: 809.159
• InChiKey: AIOJAQUWVIEMON-FKGCXKJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  55
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  209
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  十四胺 在 sodium methylate 、 二正丁基氧化锡 、 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 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 N-[(S)-1-tetradecylcarbamoyl-2-(3-sulfo-β-D-galactopyranosyl)oxyethyl]hexadecanamide
  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

文献信息

• Studies on scavenger receptor inhibitors. Part 1: synthesis and structure–activity relationships of novel derivatives of sulfatides
  作者：Kazuya Yoshiizumi、Fumio Nakajima、Rika Dobashi、Noriyasu Nishimura、Shoji Ikeda

  DOI：10.1016/s0968-0896(02)00120-7

  日期：2002.8

  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.