Icosanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide | 164988-81-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: Icosanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide
• 英文别名: N-[(E,2S,3R)-3-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]icosanamide
• CAS: 164988-81-2
• 化学式: C₇₂H₁₀₉NO₈
• 分子量: 1116.66
• InChiKey: KLKDAJNLWWFLBU-YIHUQUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21
• 重原子数：
  81
• 可旋转键数：
  49
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Icosanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide 在 palladium on barium sulfate 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以87%的产率得到(2S,3R)-1-O-(α-D-galactopyranosyl)-2-(N-icosanoylamino)-1,3-octadecanediol
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018
• 作为产物：
  描述：

  D-鞘氨醇 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 Icosanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide
  参考文献：
  名称：

  Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice

  摘要：

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.

  DOI：

  10.1021/jm00012a018

文献信息

• Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice
  作者：Masahiro Morita、Kazuhiro Motoki、Kohji Akimoto、Takenori Natori、Teruyuki Sakai、Eiji Sawa、Kazuo Yamaji、Yasuhiko Koezuka、Eiichi Kobayashi、Hideaki Fukushima

  DOI：10.1021/jm00012a018

  日期：1995.6

  Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2-[N-((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S;4R)-1-O-(alpha-D-galactopyranosyl)2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.