(1S,2S)-2-fluoro-N-[(1,1-²H₂)prop-2-yn-1-yl]indan-1-amine | 1401071-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2S)-2-fluoro-N-[(1,1-²H₂)prop-2-yn-1-yl]indan-1-amine
• 英文别名: (1S,2S)-N-(1,1-dideuterioprop-2-ynyl)-2-fluoro-2,3-dihydro-1H-inden-1-amine
• CAS: 1401071-36-0
• 化学式: C₁₂H₁₂FN
• 分子量: 191.217
• InChiKey: NYDFHNRLRLOAGB-LZKYEKCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 磺酰氯 、 potassium carbonate 、 三乙胺 、 cesium fluoride 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 133.5h， 生成 (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

文献信息

• 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.