(2S,3R,2'S,3'E)-2-N-(2'-methoxymethoxy-3'-octadecenoyl)-[2-amino-octadecan-1,3-diol] | 518027-44-6

• 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: (2S,3R,2'S,3'E)-2-N-(2'-methoxymethoxy-3'-octadecenoyl)-[2-amino-octadecan-1,3-diol]
• 英文别名: (E,2S)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]-2-(methoxymethoxy)octadec-3-enamide
• CAS: 518027-44-6
• 化学式: C₃₈H₇₅NO₅
• 分子量: 626.017
• InChiKey: HXZMQAYNOATDQR-GBPFXZCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  44
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,2'S,3'E)-2-N-(2'-methoxymethoxy-3'-octadecenoyl)-[2-amino-octadecan-1,3-diol] 在 三氟化硼乙醚 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 以72%的产率得到(2S,2'S,3R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-<2-amino-1,3-dihydroxyoctadecane>
  参考文献：
  名称：

  Total Syntheses of Symbioramide Derivatives from l-Serine and Their Antileukemic Activities

  摘要：

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.

  DOI：

  10.1021/jo0206824
• 作为产物：
  描述：

  D-赤式-二氢-D-鞘氨醇 在 4-甲基苯磺酸吡啶 、 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 (2S,3R,2'S,3'E)-2-N-(2'-methoxymethoxy-3'-octadecenoyl)-[2-amino-octadecan-1,3-diol]
  参考文献：
  名称：

  Total Syntheses of Symbioramide Derivatives from l-Serine and Their Antileukemic Activities

  摘要：

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.

  DOI：

  10.1021/jo0206824

文献信息

• Total Syntheses of Symbioramide Derivatives from <scp>l</scp>-Serine and Their Antileukemic Activities
  作者：Hideki Azuma、Ryoko Takao、Hayato Niiro、Keiji Shikata、Seizo Tamagaki、Taro Tachibana、Kenji Ogino

  DOI：10.1021/jo0206824

  日期：2003.4.1

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.