Radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines and its application to new radiotracers for NR2B NMDA receptor visualization was written by Koudih, Radouane;Gilbert, Gwenaelle;Dhilly, Martine;Abbas, Ahmed;Barre, Louisa;Debruyne, Daniele;Sobrio, Franck. And the article was included in Organic & Biomolecular Chemistry in 2012.Safety of (3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate The following contents are mentioned in the article:
In order to develop a novel and useful building block for the development of radiotracers for positron emission tomog. (PET), we studied the radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines. Indeed, 3-fluoropiperidine became a useful building block in medicinal chem. for the pharmacomodulation of piperidine-containing compounds The radiofluorination was studied on substituted piperidines with electron-donating and electron-withdrawing N-substituents. In the instance of electron-donating N-substituents such as benzyl or Bu, configuration retention and satisfactory fluoride-18 incorporation yields up to 80% were observed In the case of electron-withdrawing N-substituents leading to carbamate or amide functions, the incorporation yields depend on the 4-susbtitutent (2 to 63%). The radiolabelling of this building block was applied to the automated radiosynthesis of NR2B NMDA receptor antagonists and effected by a com. available radiochem. module. The in vivo evaluation of three radiotracers demonstrated minimal brain uptakes incompatible with the imaging of NR2B NMDA receptors in the living brain. Nevertheless, moderate radiometabolism was observed and, in particular, no radiodefluorination was observed which demonstrates the stability of the 3-position of the fluorine-18 atom. In conclusion, the 1,4-disubstituted 3-[18F]fluoropiperidine moiety could be of value in the development of other radiotracers for PET even if the evaluation of the NR2B NMDA receptor antagonists failed to demonstrate satisfactory properties for PET imaging of this receptor. This study involved multiple reactions and reactants, such as (3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (cas: 882033-93-4Safety of (3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate).
(3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (cas: 882033-93-4) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Safety of (3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem