N-[(S)-1-tetradecylcarbamoyl-2-(β-D-galactopyranosyl)oxyethyl]hexadecanamide | 485323-65-7

• 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-(β-D-galactopyranosyl)oxyethyl]hexadecanamide
• 英文别名: N-stearoyl-O-(β-D-galactopyranosyl)-L-serine myristylamide；N-[(2S)-1-oxo-1-(tetradecylamino)-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]octadecanamide
• CAS: 485323-65-7
• 化学式: C₄₁H₈₀N₂O₈
• 分子量: 729.095
• InChiKey: NIFGKMZTLCTYNF-KZFWZVKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  51
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(S)-1-tetradecylcarbamoyl-2-(β-D-galactopyranosyl)oxyethyl]hexadecanamide 在 二正丁基氧化锡 、 三乙胺三氧化硫 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 反应 68.0h， 以5.7%的产率得到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
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium dihydroxide 吡啶 、 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(S)-1-tetradecylcarbamoyl-2-(β-D-galactopyranosyl)oxyethyl]hexadecanamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes

  摘要：

  We have established an efficient synthesis of mimics of beta-galactosylceramide (beta-GalCer) increasing a beta-glucocerebrosidase (beta-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic beta-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of beta-GlcCer'ase function in vitro and reduced the transepidermal water loss (TEWL) level in a UVB-induced barrier disrupted mice model. These findings indicated that compound 6e could be useful for cosmetics and medicines to improve skin barrier function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00006-4

文献信息

• Synthesis of Sulfated Cerebroside Analogs Having Mimicks of Ceramide and Their Anti-human Immunodeficiency Virus Type 1 Activities.
  作者：Hiroyuki YOSHIDA、Kiyoshi IKEDA、Kazuo ACHIWA、Hiroo HOSINO

  DOI：10.1248/cpb.43.594

  日期：——

  Various sulfated cerebroside analogs, which are mimicks of cerebroside, have been prepared from per-O-acetylated D-glucose, per-O-acetylated D-galactose, and per-O-acetylated D-lactose with ethyleneglycol dodecyl ether, 3-docosyloxy-1-propanol, 2-hydroxymethyl-1, 3-O-dimyristyl-1, 3-propanediol, and L-serine diamide derivatives as ceramide moieties. The synthesized sulfated glycolipids showed anti-HIV-1 activities.

  以过-O-乙酰化 D-葡萄糖、过-O-乙酰化 D-半乳糖和过-O-乙酰化 D-乳糖为神经酰胺分子，以乙二醇十二烷基醚、3-二十二烷氧基-1-丙醇、2-羟甲基-1，3-O-二肉豆蔻基-1，3-丙二醇和 L-丝氨酸二酰胺衍生物为神经酰胺分子，制备了各种硫酸化脑苷脂类似物，它们是脑苷脂的模拟物。合成的硫酸化糖脂具有抗 HIV-1 活性。
• 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.
• Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes
  作者：Kyoko Fukunaga、Masahiro Yoshida、Fumio Nakajima、Rie Uematsu、Mariko Hara、Shintaro Inoue、Hirosato Kondo、Shin-Ichiro Nishimura

  DOI：10.1016/s0960-894x(03)00006-4

  日期：2003.3

  We have established an efficient synthesis of mimics of beta-galactosylceramide (beta-GalCer) increasing a beta-glucocerebrosidase (beta-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic beta-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of beta-GlcCer'ase function in vitro and reduced the transepidermal water loss (TEWL) level in a UVB-induced barrier disrupted mice model. These findings indicated that compound 6e could be useful for cosmetics and medicines to improve skin barrier function. (C) 2003 Elsevier Science Ltd. All rights reserved.