(Z)-1-[(t-butyldimethylsilyl)oxy]-18-[2-(tetrahydropyranyl)oxy]-9-octadecene | 885022-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-1-[(t-butyldimethylsilyl)oxy]-18-[2-(tetrahydropyranyl)oxy]-9-octadecene
• 英文别名: Z-1-(tert-butyldimethylsilyl)oxy-18-(2-tetrahydropyranyl)oxy-9-octadecene；tert-butyl-dimethyl-[(Z)-18-(oxan-2-yloxy)octadec-9-enoxy]silane
• CAS: 885022-64-0
• 化学式: C₂₉H₅₈O₃Si
• 分子量: 482.863
• InChiKey: IPPFGSINMJLULF-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  33
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-[(t-butyldimethylsilyl)oxy]-18-[2-(tetrahydropyranyl)oxy]-9-octadecene 在 lithium hydroxide 、 重铬酸吡啶 、 乙醇 、 四溴化碳 、 四丁基氟化铵 、 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 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.42h， 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 、 正丁基锂 、 nickel diacetate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 18.17h， 生成 (Z)-1-[(t-butyldimethylsilyl)oxy]-18-[2-(tetrahydropyranyl)oxy]-9-octadecene
  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

• Synthesis of new 123I-labeled free fatty acids analogues and first evaluation as potential tracers for SPECT imaging to elucidate fatty acid flux in mouse
  作者：Ali Ouadi、Caroline Habold、Murielle Keller、Virgile Bekaert、David Brasse

  DOI：10.1039/c3ra43092h

  日期：——

  The aim of our study was to synthesize new radiotracers for in vivo imaging to examine the metabolic fate of fatty acids according to their unsaturation degree. Three different fatty acids of the 18-carbon series have been synthesized, labeled with 123I, and their biodistribution has been evaluated in mice in vivo. The main result shows a different distribution pattern of the fatty acids according to their degree of unsaturation between the white adipose tissue and the muscles, which is coherent with previous studies using stable isotopes.

  我们研究的目的是合成用于体内成像的新型放射性痕量物质，以根据脂肪酸的不饱和程度研究其代谢命运。我们合成了三种不同的 18 碳脂肪酸，用 123I 标记，并在小鼠体内对它们的生物分布进行了评估。主要结果显示，根据脂肪酸的不饱和程度，它们在白色脂肪组织和肌肉之间的分布模式有所不同，这与之前使用稳定同位素进行的研究结果一致。
• 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.