(Z)-18-[2-(tetrahydropyranyl)oxy]-9-octadecenoic acid methyl ester | 885022-68-4

• 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: (Z)-18-[2-(tetrahydropyranyl)oxy]-9-octadecenoic acid methyl ester
• 英文别名: methyl (Z)-18-(oxan-2-yloxy)octadec-9-enoate
• CAS: 885022-68-4
• 化学式: C₂₄H₄₄O₄
• 分子量: 396.611
• InChiKey: KRKXPQWXCCNXRS-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-18-[2-(tetrahydropyranyl)oxy]-9-octadecenoic acid methyl ester 在 lithium hydroxide 、 乙醇 、 四溴化碳 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.67h， 生成 (Z)-18-bromo-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]octadec-9-enamide
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 nickel diacetate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.92h， 生成 (Z)-18-[2-(tetrahydropyranyl)oxy]-9-octadecenoic acid methyl ester
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l

文献信息

• Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake
  作者：Aniello Schiano Moriello、Laurence Balas、Alessia Ligresti、Maria Grazia Cascio、Thierry Durand、Enrico Morera、Giorgio Ortar、Vincenzo Di Marzo

  DOI：10.1021/jm051226l

  日期：2006.4.1

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.