(S)-N,O-bis-tert-butoxycarbonyl-4-(4-hydroxybenzoyl)phenylalaninol acetic acid ester | 885022-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N,O-bis-tert-butoxycarbonyl-4-(4-hydroxybenzoyl)phenylalaninol acetic acid ester
• 英文别名: [(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]benzoyl]phenyl]propyl] acetate
• CAS: 885022-12-8
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: FKTJEKLWOMDELV-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-N,O-bis-tert-butoxycarbonyl-4-(4-hydroxybenzoyl)phenylalaninol acetic acid ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以98%的产率得到(S)-N-tert-butoxycarbonyl-4-(4-hydroxybenzoyl)phenylalaninol
  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：

  O-tert-butoxycarbonyl-4-hydroxyiodobenzene 、 (S)-N-tert-butoxycarbonyl-4-trimethylstannylphenylalaninol acetic acid ester 、 一氧化碳 在 三苯基膦 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以52%的产率得到(S)-N,O-bis-tert-butoxycarbonyl-4-(4-hydroxybenzoyl)phenylalaninol acetic acid 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