anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester | 439090-04-7

• 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: anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester
• CAS: 439090-04-7
• 化学式: C₂₂H₃₃NO₅
• 分子量: 391.508
• InChiKey: OUBYDIKUMUKLFP-VVOJOOEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 作用下， 生成 anti-1-[N-(tert-butoxycarbonyl)amino]-3-mesyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester
  参考文献：
  名称：

  Synthesis of 2,6-dideoxy-2-fluoro-6-[18F]-fluoro-?-D-glucopyranosyl fluoride (2,6FGF) as a potential imaging probe for glucocerebrosidase

  摘要：

  我们之前合成了2-deoxy-2-[18F]-fluoro-β-mannosyl [18F]-氟化物，并证明其作为根肿瘤农杆菌β-葡萄糖苷酶的机制抑制剂。在体内实验中表明该化合物会部分水解，生成2-deoxy-2-fluoro-mannose，该物质可以被磷酸化并被困在细胞内。我们现在报告合成了另一种在6位标记有18F的2-fluoro糖苷，这样在糖苷水解过程中标签不会丢失，并且该化合物无法被磷酸化。机制基础的糖苷酶抑制剂2,6-脱氧-2-氟-6-[18F]-氟化β-D-葡萄糖吡喃糖苷氟化物（2,6FGF）以69%的总体化学产率和9%的放射化学产率（已校正衰变）合成，作为糖苷酶的潜在成像探针。版权 © 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.466
• 作为产物：
  描述：

  3-(benzyloxymethyl)-2,2-dichlorocyclobutanone 在 sodium hydroxide 、 碳酸氢铵 、 氯化铵 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 生成 anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester
  参考文献：
  名称：

  Synthesis of 2,6-dideoxy-2-fluoro-6-[18F]-fluoro-?-D-glucopyranosyl fluoride (2,6FGF) as a potential imaging probe for glucocerebrosidase

  摘要：

  我们之前合成了2-deoxy-2-[18F]-fluoro-β-mannosyl [18F]-氟化物，并证明其作为根肿瘤农杆菌β-葡萄糖苷酶的机制抑制剂。在体内实验中表明该化合物会部分水解，生成2-deoxy-2-fluoro-mannose，该物质可以被磷酸化并被困在细胞内。我们现在报告合成了另一种在6位标记有18F的2-fluoro糖苷，这样在糖苷水解过程中标签不会丢失，并且该化合物无法被磷酸化。机制基础的糖苷酶抑制剂2,6-脱氧-2-氟-6-[18F]-氟化β-D-葡萄糖吡喃糖苷氟化物（2,6FGF）以69%的总体化学产率和9%的放射化学产率（已校正衰变）合成，作为糖苷酶的潜在成像探针。版权 © 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.466

文献信息

• Synthesis of <i>syn</i>- and <i>anti</i>-1-Amino-3-[¹⁸F]fluoromethyl-cyclobutane-1-carboxylic Acid (FMACBC), Potential PET Ligands for Tumor Detection
  作者：Laurent Martarello、Jonathan McConathy、Vernon M. Camp、Eugene J. Malveaux、Nicholas E. Simpson、Chiab P. Simpson、Jeffrey J. Olson、Geoffrey D. Bowers、Mark M. Goodman

  DOI：10.1021/jm010242p

  日期：2002.5.1

  syn- and anti-1-Amino-3-[F-18]fluoromethyl-cyclobutane-1-carboxylic acid (FMACBC, 16 and 17), analogues of anti-1-amino-3-[F-18]fluorocyclobutyl-1-carboxylic acid (FACBC), were prepared to evaluate the contributions of C-3 substitution and configuration on the uptake of these radiolabeled amino acids in a rodent model of brain tumors. Radiofluorinated targets [F-18]16 and [18F]17 were prepared by no-carrier-added radiofluorination from their corresponding methanesulfonyl esters 12 and 13, respectively, with decay-corrected radiochemical yields of 30% for [F-18]16 and 20% for [F-18]17. In amino acid transport assays performed in vitro using 9L gliosarcoma cells, both [F-18]16 and [F-18]17 were substrates for L type amino acid transport, while [F-18]17 but not [F-18]16 was a substrate for A type transport. Biodistribution studies in normal Fischer rats with [F-18]16 and [F-18]17 showed high uptake of radioactivity (>2.0% dose/g) in the pancreas while other tissues studied, including liver, heart, lung, kidney, blood, muscle, and testis, showed relatively low uptake of radioactivity (<1.0% dose/g). In rats implanted intracranially with 9L gliosarcoma cells, the retention of radioactivity in tumor tissue was high at 5, 60, and 120 min after intravenous injection of [F-18]16 and [F-18]17 while the uptake of radioactivity in brain tissue contralateral to the tumor remained low (<0.3% dose/g). Ratios of tumor uptake to normal brain uptake for [F-18]16 were 7.5:1, 7:1, and 5:1 at 5, 60, and 120 min, respectively, while for [18F]17 the ratios were 7.5:1, 9:1, and 9:1 at the same time points. This work demonstrates that like anti-[F-18]FACBC, [F-18]16 and [F-18]17 are excellent candidates for imaging brain tumors.