tert-butyl N-(tert-butoxycarbonyl)homocysteinate

• 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: tert-butyl N-(tert-butoxycarbonyl)homocysteinate
• 英文别名: tert-butyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-sulfanylbutanoate
• 化学式: C₁₃H₂₅NO₄S
• 分子量: 291.412
• InChiKey: AFSKWXGSKKCBDW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(tert-butoxycarbonyl)homocysteinate 在 potassium [¹⁸F]fluoride 、 potassium oxalate 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.17h， 生成 tert-butyl D-(18)F-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：

  di(tert-butyl) N,N'-bis(tert-butoxycarbonyl)homocystinate 在 三丁基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到tert-butyl N-(tert-butoxycarbonyl)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

文献信息

• Nitric oxide synthase inhibitors
  申请人：——

  公开号：US20020010366A1

  公开（公告）日：2002-01-24

  The present invention relates to novel amidino compound of formula (I). 1 to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use as selective inhibitors of inducible nitric oxide synthase.

  本发明涉及一种新的式（I）的酰胺化合物，其制备方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是作为诱导型一氧化氮合酶的选择性抑制剂的用途。
• [EN] RADIOLABELED FLUORINE DERIVATIVES OF METHIONINE<br/>[FR] DÉRIVÉS DE LA MÉTHIONINE RADIOMARQUÉS AU FLUOR
  申请人：CRC FOR BIOMEDICAL IMAGING DEV

  公开号：WO2010108210A1

  公开（公告）日：2010-09-30

  The invention provides compound which is an 18F-radiolabelled S-propylhomocysteine or a derivative thereof. The compound has an enantiomeric purity of at least about 90%. 18F- radiolabelled S-propylhomocysteine may be made by treating an N-protected ester of a substituted S-propylhomocysteine with a complexed F" salt in the presence of a base to form a protected product and then deprotecting the protected product to form the 18F- radiolabelled S-propylhomocysteine. In this method the N-protected ester has a leaving group on the S-propyl group and has an enantiomeric purity of at least about 90%. The base should be such that it does not cause racemisation of the protected product.

  该发明提供了一种18F-放射标记的S-丙基同型半胱氨酸化合物或其衍生物。该化合物的对映纯度至少为约90%。18F-放射标记的S-丙基同型半胱氨酸可以通过处理取代的S-丙基同型半胱氨酸的N-保护酯与复合F"盐在碱存在下形成保护产物，然后去保护产物以形成18F-放射标记的S-丙基同型半胱氨酸来制备。在这种方法中，N-保护酯在S-丙基基团上有一个离去基团，并且其对映纯度至少为约90%。碱应该是不会导致保护产物发生外消旋的碱。
• [EN] NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS DE MONOXYDE D'AZOTE SYNTHETASE
  申请人：GLAXO GROUP LIMITED

  公开号：WO1998030537A1

  公开（公告）日：1998-07-16

  (EN) The present invention relates to novel amidino compounds of formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use as selective inhibitors of inducible nitric oxide synthase.(FR) L'invention concerne de nouveaux composés d'amidino représentés par la formule (I), un procédé servant à les préparer, des compositions pharmaceutiques les contenant et leur utilisation thérapeutique, en particulier, en tant qu'inhibiteurs sélectifs de la monoxyde d'azote synthétase inductible.

  本发明涉及一种新的化合物，为公式（I）所示的酰胺化合物，以及制备它们的方法，包含它们的药物组合物和它们作为选择性抑制诱导型一氧化氮合酶的治疗用途，特别是作为选择性抑制诱导型一氧化氮合酶的药物。
• Radiolabeled Fluorine Derivatives of Methionine
  申请人：Katsifis Andrew

  公开号：US20120093726A1

  公开（公告）日：2012-04-19

  The invention provides compound which is an 18 F-radiolabelled S-propylhomocysteine or a derivative thereof. The compound has an enantiomeric purity of at least about 90%. 18 F-radiolabelled S-propylhomocysteine may be made by treating an N-protected ester of a substituted S-propylhomocysteine with a complexed F″ salt in the presence of a base to form a protected product and then deprotecting the protected product to form the 18 F-radiolabelled S-propylhomocysteine. In this method the N-protected ester has a leaving group on the S-propyl group and has an enantiomeric purity of at least about 90%. The base should be such that it does not cause racemisation of the protected product.

  本发明提供了一种化合物，该化合物是18F放射性标记的S-丙基同型半胱氨酸或其衍生物。该化合物具有至少约90％的对映异构体纯度。可以通过在碱存在下用复合的F″盐处理替代的S-丙基同型半胱氨酸的N-保护酯以形成受保护的产物，然后去保护以形成18F放射性标记的S-丙基同型半胱氨酸来制备18F放射性标记的S-丙基同型半胱氨酸。在该方法中，N-保护酯在S-丙基基团上具有离去基，并且具有至少约90％的对映异构体纯度。碱应该是不会引起受保护产物的旋光异构化的碱。
• NITRIC OXIDE SYNTHASE INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP0958277B1

  公开（公告）日：2001-11-21