[(Z)-12-[[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-[4-[tert-butyl(diphenyl)silyl]oxyphenyl]propan-2-yl]amino]-12-oxododec-3-enyl] 2-azido-5-iodobenzoate | 928122-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(Z)-12-[[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-[4-[tert-butyl(diphenyl)silyl]oxyphenyl]propan-2-yl]amino]-12-oxododec-3-enyl] 2-azido-5-iodobenzoate
• CAS: 928122-38-7
• 化学式: C₆₀H₇₁IN₄O₅Si₂
• 分子量: 1111.32
• InChiKey: VLSFHIRPUFRGID-PLUZKJAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.31
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(Z)-12-[[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-[4-[tert-butyl(diphenyl)silyl]oxyphenyl]propan-2-yl]amino]-12-oxododec-3-enyl] 2-azido-5-iodobenzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以75%的产率得到[(Z)-12-[[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]amino]-12-oxododec-3-enyl] 2-azido-5-iodobenzoate
  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：

  di-O-tert-butyldiphenylsilyl-(S)-tyrosinol 在 N-甲基吗啉 、 甲醇 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.5h， 生成 [(Z)-12-[[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-[4-[tert-butyl(diphenyl)silyl]oxyphenyl]propan-2-yl]amino]-12-oxododec-3-enyl] 2-azido-5-iodobenzoate
  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