1146971-53-0

Upstream product

• 1146971-51-8 (S)-2-(methyl(prop-2-ynyl)amino)-3-phenylpropan-1-ol 
• 717128-19-3 (S)-2-(N,N-diallylamino)-3-phenylpropan-1-ol 
• 3182-95-4 L-Phenylalaninol 
• 50-00-0 formaldehyd 
• 77210-51-6 (S)-1-fluoro-3-phenylpropan-2-ammonium chloride 
• 84773-29-5 (S)-(+)-2-(N-methylamino)-3-phenylpropanol 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 1146971-52-9 methanesulfonic acid (S)-2-(methyl-prop-2-ynyl-amino)-3-phenylpropyl ester 

Relevant academic research and scientific papers

Nucleophilic Fluorination and Radiofluorination via Aziridinium Intermediates: N-Substituent Influence, Unexpected Regioselectivity, and Differences between Fluorine-19 and Fluorine-18

The efficient dehydrofluorination and radiofluorination of N,N-disubstituted-β-aminoalcohols through an anchimeric-assisted mechanism was developed. An investigation into the influence of N-substituents on the ring opening of the aziridinium intermediate indicated differences in the isomeric ratio and the yields of fluorinated products obtained from N,N-disubstituted-phenylalaninol. This influence was substantial for 18F-radiofluorination, with yields varying from 0 to 71% at room temperature (RT). Although no significant effects were observed in the fluorine-19 chemistry when the reaction was heated to 90 °C, considerable changes appeared during radiofluorination. In the latter case, the radiochemical yields increased, and degradation of the 2-fluoro-propan-1-amine isomer (b) occurred, leading to a regiospecific reaction in the radiolabeling of [18F]-fluorodeprenyl. This method involving nucleophilic radiofluorination at RT was successfully applied to the radiolabeling of [18F]-2-fluoroethylamines in which the influence of the N-substituent was also observed.

Synthesis of three novel fluorine-18 labeled analogues of l -deprenyl for Positron Emission Tomography (PET) studies of Monoamine Oxidase B (MAO-B)

The aim in this project was to synthesize and to study fluorine-18 labeled analogues of l-deprenyl which bind selectively to the enzyme monoamine oxidase B (MAO-B). Three fluorinated l-deprenyl analogues have been generated in multistep organic syntheses. The most promising fluorine-18 compound N-[(2S)-1-[18F]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine (4c) was synthesized by a one-step fluorine-18 nucleophilic substitution reaction. Autoradiography on human brain tissue sections demonstrated specific binding for compound 4c to brain regions known to have a high content of MAO-B. In addition, the corresponding nonradioactive fluorine-19 compound (13) inhibited recombinant human MAO-B with an IC50 of 170.5 ±29 nM but did not inhibit recombinant human MAO-A (IC50 > 2000 nM), demonstrating its specificity. Biodistribution of 4c in mice showed high initial brain uptake leveling at 5.2 ±0.04%ID/g after 2 min post injection. In conclusion, compound 4c is a specific inhibitor of MAO-B with high initial brain uptake in mice and is, therefore, a candidate for further investigation in PET.

COMPOUNDS FOR USE IN IMAGING, DIAGNOSING, AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS

This invention relates to novel compounds suitable for labelling or already labelled by 18F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds