(3aS,8aR)-3-[(1,1-²H₂)prop-2-yn-1-yl]-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole 2,2-dioxide | 1401071-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aS,8aR)-3-[(1,1-²H₂)prop-2-yn-1-yl]-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole 2,2-dioxide
• 英文别名: (3aR,8bS)-1-(1,1-dideuterioprop-2-ynyl)-4,8b-dihydro-3aH-indeno[1,2-d]oxathiazole 2,2-dioxide
• CAS: 1401071-35-9
• 化学式: C₁₂H₁₁NO₃S
• 分子量: 251.274
• InChiKey: SISGTSXVMIDKEJ-KZRUWGSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,8aR)-3-[(1,1-²H₂)prop-2-yn-1-yl]-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole 2,2-dioxide 在 cesium fluoride 、 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 、 乙醇 为溶剂， 反应 61.5h， 以74%的产率得到(1S,2S)-2-fluoro-N-[(1,1-²H₂)prop-2-yn-1-yl]indan-1-amine
  参考文献：
  名称：

  [EN] COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM
  [FR] COMPOSÉ DESTINÉ À ÊTRE UTILISÉ EN IMAGERIE, DIAGNOSTIC ET/OU TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本发明涉及适合用18F标记的新型化合物，以及相应的18F标记化合物本身，其19F-氟化类似物及其用作参考标准的用途，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒，以及用于正电子发射断层扫描（PET）的这种化合物、组合物或试剂盒的用途。

  公开号：

  WO2012126913A1
• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 磺酰氯 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (3aS,8aR)-3-[(1,1-²H₂)prop-2-yn-1-yl]-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole 2,2-dioxide
  参考文献：
  名称：

  [EN] COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM
  [FR] COMPOSÉ DESTINÉ À ÊTRE UTILISÉ EN IMAGERIE, DIAGNOSTIC ET/OU TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本发明涉及适合用18F标记的新型化合物，以及相应的18F标记化合物本身，其19F-氟化类似物及其用作参考标准的用途，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒，以及用于正电子发射断层扫描（PET）的这种化合物、组合物或试剂盒的用途。

  公开号：

  WO2012126913A1

文献信息

• [EN] COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM<br/>[FR] COMPOSÉ DESTINÉ À ÊTRE UTILISÉ EN IMAGERIE, DIAGNOSTIC ET/OU TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL
  申请人：PIRAMAL IMAGING SA

  公开号：WO2012126913A1

  公开（公告）日：2012-09-27

  This invention relates to novel compounds suitable for labelling by 18F and the corresponding 18F labelled compounds themselves, 19F-fluorinated analogues thereof and their use as reference standards, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by Positron Emission Tomography (PET).

  本发明涉及适合用18F标记的新型化合物，以及相应的18F标记化合物本身，其19F-氟化类似物及其用作参考标准的用途，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒，以及用于正电子发射断层扫描（PET）的这种化合物、组合物或试剂盒的用途。
• COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM
  申请人：Thiele Andrea

  公开号：US20140193338A1

  公开（公告）日：2014-07-10

  This invention relates to novel compounds suitable for labelling by 18 F and the corresponding 18 F labelled compounds themselves, 19 F-fluorinated analogues thereof and their use as reference standards, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by Positron Emission Tomography (PET).
• Development of a novel fluorine-18 labeled deuterated fluororasagiline ([18F]fluororasagiline-D2) radioligand for PET studies of monoamino oxidase B (MAO-B)
  作者：S. Nag、L. Lehmann、G. Kettschau、M. Toth、T. Heinrich、A. Thiele、A. Varrone、C. Halldin

  DOI：10.1016/j.bmc.2013.08.019

  日期：2013.11

  The objective of this study was to synthesize and evaluate a novel fluorine-18 labeled deuterium substituted analogue of rasagiline (9, [F-18]fluororasagiline-D-2) as a potential PET radioligand for studies of monoamine oxidase B (MAO-B).The precursor compound (6) and reference standard (7) were synthesized in multi-step syntheses. Radiolabeling of 9 was accomplished by a two-step synthesis, compromising a nucleophilic substitution followed by hydrolysis of the sulfamidate group. The incorporation radiochemical yield from fluorine-18 fluoride was higher than 30%, the radiochemical purity was >99% and the specific radioactivity was >160 GBq/mu mol at the time of administration.In vitro compound 7 inhibited the MAO-B activity with an IC50 of 173.0 +/- 13.6 nM. The MAO-A activity was inhibited with an IC50 of 9.9 +/- 1.1 mu M. The fluorine-18 version 9 was characterized in the cynomolgus monkey brain where a high brain uptake was found (275% SUV at 4 min). There was a higher uptake in the striatum and thalamus compared to the cortex and cerebellum. A pronounced blocking effect (50% decrease) was observed in the specific brain regions after administration of L-deprenyl (0.5 mg/kg) 30 min prior to the administration of 9. Radiometabolite studies demonstrated 40% of unchanged radioligand at 90 min post injection.An efficient radiolabeling of 9 was successfully established and in the monkey brain 9 binds to MAO-B rich regions and its binding is blocked by the selective MAO-B compound L-deprenyl. The radioligand 9 is a potential candidate for human PET studies. (C) 2013 Elsevier Ltd. All rights reserved.