3-benzyloxy-2-[N-(tert-butoxycarbonyl)methylamino]-2-methylpropanoic acid tert-butyl ester | 438574-24-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-benzyloxy-2-[N-(tert-butoxycarbonyl)methylamino]-2-methylpropanoic acid tert-butyl ester
• 英文别名: Tert-butyl 2-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-phenylmethoxypropanoate
• CAS: 438574-24-4
• 化学式: C₂₁H₃₃NO₅
• 分子量: 379.497
• InChiKey: OSZWTGFONBFRBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-2-[N-(tert-butoxycarbonyl)methylamino]-2-methylpropanoic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 2-[N-(tert-butoxycarbonyl)methylamino]-3-hydroxy-2-methylpropanoic acid tert-butyl ester
  参考文献：
  名称：

  McConathy, J.; Martarello, L.; Goodman, M. M., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S376 - S378

  摘要：

  DOI：
• 作为产物：
  描述：

  苄氧基丙酮 在 sodium hydroxide 、 碳酸氢铵 、 sodium hydride 、 氯化铵 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 3-benzyloxy-2-[N-(tert-butoxycarbonyl)methylamino]-2-methylpropanoic acid tert-butyl ester
  参考文献：
  名称：

  Radiolabeled Amino Acids for Tumor Imaging with PET:  Radiosynthesis and Biological Evaluation of 2-Amino-3-[¹⁸F]fluoro-2-methylpropanoic Acid and 3-[¹⁸F]Fluoro-2-methyl-2-(methylamino)propanoic Acid

  摘要：

  Novel radiopharmaceuticals, including amino acids, that target neoplasms through their altered metabolic states have shown promising results in preclinical and clinical studies. Two fluorinated analogues of alpha-aminoisobutyric acid, 2-amino-3-fluoro-2-methylpropanoic acid (FAMP) and 3-fluoro-2-methyl-2-(methylamino)propanoic acid (N-MeFAMP), have been radiolabeled with fluorine-18, characterized in amino acid uptake assays, and evaluated in vivo in normal rats and a rodent tumor model. The key steps in the syntheses of both radiotracers involved the preparation of cyclic sulfamidate precursors. Radiosyntheses of both [F-18]FAMP and [F-18]N-MeFAMP via no-carrier-added nucleophilic substitution provided high yields (>78% decay-corrected) in high radiochemical purity (>99%). Amino acid transport assays using 9L gliosarcoma cells demonstrated that both compounds are substrates for the A type amino acid transport system, with [F-18]N-MeFAMP showing higher specificity than [F-18] FAMP for A type transport. Tissue distribution studies in normal Fischer rats and Fischer rats implanted intracranially with 9L gliosarcoma tumor cells were also performed. At 60 min postinjection, the tumor vs normal brain ratio of radioactivity was 36:1 in animals receiving [F-18] FAMP and 104:1 in animals receiving [F-18]N-MeFAMP. On the basis of these studies, both [F-18]FAMP and [F-18]N-MeFAMP are promising imaging agents for the detection of intracranial neoplasms via positron emission tomography.

  DOI：

  10.1021/jm010241x

文献信息

• McConathy, J.; Martarello, L.; Goodman, M. M., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S376 - S378
  作者：McConathy, J.、Martarello, L.、Goodman, M. M.

  DOI：——

  日期：——
• Radiolabeled Amino Acids for Tumor Imaging with PET:  Radiosynthesis and Biological Evaluation of 2-Amino-3-[¹⁸F]fluoro-2-methylpropanoic Acid and 3-[¹⁸F]Fluoro-2-methyl-2-(methylamino)propanoic Acid
  作者：Jonathan McConathy、Laurent Martarello、Eugene J. Malveaux、Vernon M. Camp、Nicholas E. Simpson、Chiab P. Simpson、Geoffrey D. Bowers、Jeffrey J. Olson、Mark M. Goodman

  DOI：10.1021/jm010241x

  日期：2002.5.1

  Novel radiopharmaceuticals, including amino acids, that target neoplasms through their altered metabolic states have shown promising results in preclinical and clinical studies. Two fluorinated analogues of alpha-aminoisobutyric acid, 2-amino-3-fluoro-2-methylpropanoic acid (FAMP) and 3-fluoro-2-methyl-2-(methylamino)propanoic acid (N-MeFAMP), have been radiolabeled with fluorine-18, characterized in amino acid uptake assays, and evaluated in vivo in normal rats and a rodent tumor model. The key steps in the syntheses of both radiotracers involved the preparation of cyclic sulfamidate precursors. Radiosyntheses of both [F-18]FAMP and [F-18]N-MeFAMP via no-carrier-added nucleophilic substitution provided high yields (>78% decay-corrected) in high radiochemical purity (>99%). Amino acid transport assays using 9L gliosarcoma cells demonstrated that both compounds are substrates for the A type amino acid transport system, with [F-18]N-MeFAMP showing higher specificity than [F-18] FAMP for A type transport. Tissue distribution studies in normal Fischer rats and Fischer rats implanted intracranially with 9L gliosarcoma tumor cells were also performed. At 60 min postinjection, the tumor vs normal brain ratio of radioactivity was 36:1 in animals receiving [F-18] FAMP and 104:1 in animals receiving [F-18]N-MeFAMP. On the basis of these studies, both [F-18]FAMP and [F-18]N-MeFAMP are promising imaging agents for the detection of intracranial neoplasms via positron emission tomography.