(Boc-D-Hcy-OH)2 | 113132-85-7

• 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: (Boc-D-Hcy-OH)2
• 英文别名: N,N'-di(tert-butoxycarbonyl)homocystine；(2R,2'R)-4,4'-disulfanediylbis(2-((tert-butoxycarbonyl)amino)butanoic acid)；(2R)-4-[[(3R)-3-carboxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 113132-85-7
• 化学式: C₁₈H₃₂N₂O₈S₂
• 分子量: 468.593
• InChiKey: JXQOESIPFURHKL-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  202
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (Boc-D-Hcy-OH)2 在 三丁基膦 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 tert-butyl N-(tert-butoxycarbonyl)-S-(3-fluoropropyl)-homocysteinate
  参考文献：
  名称：

  Radiosynthesis and Biological Evaluation of l- and d-S-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography

  摘要：

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.

  DOI：

  10.1021/jm101513q
• 作为产物：
  描述：

  D-增胱氨酸 、 二碳酸二叔丁酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以100%的产率得到(Boc-D-Hcy-OH)2
  参考文献：
  名称：

  Radiosynthesis and Biological Evaluation of l- and d-S-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography

  摘要：

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.

  DOI：

  10.1021/jm101513q

文献信息

• Peripherally acting enkephalin analogs. 1. Polar pentapeptides
  作者：George W. Hardy、Lawrence A. Lowe、Pang Yih Sang、Dean S. A. Simpkin、Samuel Wilkinson、Rhonda L. Follenfant、Terence W. Smith

  DOI：10.1021/jm00400a012

  日期：1988.5

  The design, synthesis, and biological activity of a series of highly polar enkephalin-related pentapeptides are reported. These analogues incorporate structural features that exclude them from the central nervous system and thereby restrict their action to peripherally located receptors. Hydrophilic analogues were obtained by introduction of polar D-amino acid residues at position 2 and, in certain cases, by conversion of the N-terminal amino group of the Tyr residue to a guanidino function. The peptides were synthesized by classical solution methods. All compounds demonstrated in vitro opioid activity in the GPI and all were shown to possess antinociceptive activity in chemically induced writhing models. The analgesic effects were shown to be predominantly peripherally mediated by antagonism of antinociception with the peripheral antagonist N-methylnalorphine. Comparative data obtained in writhing and hot-plate tests were also supportive of a peripheral mode of action. Compound 13a, L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide (BW 443C), was identified as having a favorable pharmacological profile, indicating a high level of peripheral selectivity, and worthy of further investigation.
• HARDY, GEORGE W.;LOWE, LAWTENCE A.;SANG, PANG YIH;SIMPKIN, DEAN S. A.;WIL+, J. MED. CHEM., 31,(1988) N 5, 960-966
  作者：HARDY, GEORGE W.、LOWE, LAWTENCE A.、SANG, PANG YIH、SIMPKIN, DEAN S. A.、WIL+

  DOI：——

  日期：——
• Radiosynthesis and Biological Evaluation of <scp>l</scp>- and <scp>d</scp>-<i>S</i>-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography
  作者：Thomas Bourdier、Rachael Shepherd、Paula Berghofer、Timothy Jackson、Christopher J. R. Fookes、Delphine Denoyer、Donna S. Dorow、Ivan Greguric、Marie-Claude Gregoire、Rodney J. Hicks、Andrew Katsifis

  DOI：10.1021/jm101513q

  日期：2011.3.24

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.