[(2S)-3-methoxy-2-[methyl-[(E)-octadec-4-enoyl]amino]propyl] (2R)-2-anthracen-9-yl-2-methoxyacetate | 1360584-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [(2S)-3-methoxy-2-[methyl-[(E)-octadec-4-enoyl]amino]propyl] (2R)-2-anthracen-9-yl-2-methoxyacetate
• CAS: 1360584-04-8
• 化学式: C₄₀H₅₇NO₅
• 分子量: 631.896
• InChiKey: UYVBKFWMGLKBQJ-BSTJSVPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  46
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+)-serinolamide A 、 (-)-(R)-α-methoxy-α-(9-anthryl)acetic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以2.2 mg的产率得到[(2S)-3-methoxy-2-[methyl-[(E)-octadec-4-enoyl]amino]propyl] (2R)-2-anthracen-9-yl-2-methoxyacetate
  参考文献：
  名称：

  Cannabinomimetic Lipid from a Marine Cyanobacterium

  摘要：

  NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB, cannabinoid receptor (K(i) = 1.3 mu M, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.

  DOI：

  10.1021/np200610t

文献信息

• Cannabinomimetic Lipid from a Marine Cyanobacterium
  作者：Marcelino Gutiérrez、Alban R. Pereira、Hosana M. Debonsi、Alessia Ligresti、Vincenzo Di Marzo、William H. Gerwick

  DOI：10.1021/np200610t

  日期：2011.10.28

  NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB, cannabinoid receptor (K(i) = 1.3 mu M, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.