(S)-(9-fluorenylmethoxycarbonyl)lysine 4-methoxybenzyl ester | 1259028-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-(9-fluorenylmethoxycarbonyl)lysine 4-methoxybenzyl ester
• 英文别名: (4-methoxyphenyl)methyl (2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoate
• CAS: 1259028-73-3
• 化学式: C₂₉H₃₂N₂O₅
• 分子量: 488.583
• InChiKey: VZIFVSOVWPPPFI-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(9-fluorenylmethoxycarbonyl)lysine 4-methoxybenzyl ester 在 哌啶 、 三异丙基硅烷 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.33h， 生成 2-[3-(1-carboxy-5-(7-[1-carboxy-5-(carboxymethylpyridin-2-ylmethylamino)pentylcarbamoyl]heptanoylamino)pentyl)ureido]pentanedioic acid
  参考文献：
  名称：

  Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.

  DOI：

  10.1021/jm400823w
• 作为产物：
  描述：

  (4-methoxyphenyl)methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 对甲苯磺酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以55%的产率得到(S)-(9-fluorenylmethoxycarbonyl)lysine 4-methoxybenzyl ester
  参考文献：
  名称：

  Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)

  摘要：

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.

  DOI：

  10.1021/jm400823w

文献信息

• An expedient synthesis of orthogonally protected lysinoalanine from Aloc-protected Garner’s aldehyde
  作者：Cindy Körner、Eun-Ang Raiber、Samuel E.M. Keegan、Daniel C. Nicolau、Tom D. Sheppard、Alethea B. Tabor

  DOI：10.1016/j.tetlet.2010.09.119

  日期：2010.12

  An expedient synthesis of orthogonally protected lysinoalanine has been developed. We have prepared a novel Garner’s aldehyde derivative bearing an Aloc group; reductive amination of this aldehyde with Fmoc-Lys-OPMB gave the lysinoalanine skeleton. This was then transformed into an orthogonally protected lysinoalanine derivative suitable for the synthesis of side-chain bridged cyclic peptides by solid

  已经开发了正交保护的赖氨酸丙氨酸的简便合成方法。我们制备了带有Aloc基团的新型加纳醛衍生物。用Fmoc-Lys-OPMB还原该醛，得到赖氨酸丙氨酸骨架。然后将其转化为适于通过固相肽合成方法合成侧链桥连的环肽的正交保护的赖氨酸丙氨酸衍生物。
• Effect of Chelators on the Pharmacokinetics of ^99mTc-Labeled Imaging Agents for the Prostate-Specific Membrane Antigen (PSMA)
  作者：Sangeeta Ray Banerjee、Mrudula Pullambhatla、Catherine A. Foss、Alexander Falk、Youngjoo Byun、Sridhar Nimmagadda、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1021/jm400823w

  日期：2013.8.8

  Technetium-99m, the most commonly used radionuclide in nuclear medicine, can be attached to biologically important molecules through a variety of chelating agents, the choice of which depends upon the imaging application. The prostate-specific membrane antigen (PSMA) is increasingly recognized as an important target for imaging and therapy of prostate cancer (PCa). Three different Tc-99m-labeling methods were employed to investigate the effect of the chelator on the biodistribution and PCa tumor uptake profiles of 12 new urea-based PSMA-targeted radiotracers. This series includes hydrophilic ligands for radiolabeling with the [Tc-99m(CO)(3)](+) core (L8-L10), traditional NxSy-based chelating agents with varying charge and polarity for the Tc-99m-oxo core (L11-L18), and a Tc-99m-organohydrazine-labeled radioligand (L19). Tc-99m(I)-Tricarbonyl-labeled [Tc-99m]L8 produced the highest PSMA+ PC3 PIP to PSMA- PC3 flu tumor ratios and demonstrated the lowest retention in normal tissues including kidney after 2 h. These results suggest that choice of chelator is an important pharmacokinetic consideration in the development of Tc-99m-labeled radiopharmaceuticals targeting PSMA.