Preparation of [18F]RP 62203, a selective ligand for the study of serotonin receptors (5-HT2) by rapid “in situ” piperazine formation

Lasne, Marie‐Claire; Barré, Louisa; Huard, Cécile; Secq, B.Le; Collins, Michael R.

doi:10.1016/0969-8043(94)90188-0

Cited by 13 publications

(5 citation statements)

References 18 publications

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“…259 [ 18 F]RP62203 ([ 11 C]73, Figure 12) was prepared via a three-step route with a radiochemical yield of 5−12% (decay corrected) in 190−230 min. 260 PET imaging in the rat brain showed that the uptake of [ 11 C]73 in the neocortex was 4-fold higher than that of the cerebellum, consistent with 5-HT 2 receptor expression, and the uptake was abolished by pretreatment with ritanserin. 261 Despite the fact that [ 11 C]73 appears to be a promising radioligand for 5-HT 2 receptors, no further PET imaging in NHPs or humans was reported, probably due to its complex synthesis route.…”

Section: Pet Ligands For 5-ht 2a Receptorsmentioning

confidence: 87%

“…Biodistribution results in rats showed that [ 3 H]RP62203 had high uptake in 5-HT 2 receptor-rich brain regions like the frontal cortex with a high ratio to the cerebellum of 6–7 . [ 18 F]RP62203 ([ 11 C] 73 , Figure ) was prepared via a three-step route with a radiochemical yield of 5–12% (decay corrected) in 190–230 min . PET imaging in the rat brain showed that the uptake of [ 11 C] 73 in the neocortex was 4-fold higher than that of the cerebellum, consistent with 5-HT 2 receptor expression, and the uptake was abolished by pretreatment with ritanserin .…”

Section: Pet Ligands For 5-ht2a Receptorsmentioning

confidence: 99%

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Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Rong

Chen

et al. 2022

J. Med. Chem.

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Serotonin (5-hydroxytryptamine, 5-HT) and 5-HT receptors (5-HTRs) have crucial roles in various neuropsychiatric disorders and neurodegenerative diseases, making them attractive diagnostic and therapeutic targets. Positron emission tomography (PET) is a noninvasive nuclear molecular imaging technique and is an essential tool in clinical diagnosis and drug discovery. In this context, numerous PET ligands have been developed for "visualizing" 5-HTRs in the brain and translated into human use to study disease mechanisms and/or support drug development. Herein, we present a comprehensive repertoire of 5-HTR PET ligands by focusing on their chemotypes and performance in PET imaging studies. Furthermore, this Perspective summarizes recent 5-HTR-focused drug discovery, including biased agonists and allosteric modulators, which would stimulate the development of more potent and subtype-selective 5-HTR PET ligands and thus further our understanding of 5-HTR biology.

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Section: Pet Ligands For 5-ht 2a Receptorsmentioning

confidence: 87%

Section: Pet Ligands For 5-ht2a Receptorsmentioning

confidence: 99%

Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Rong

Chen

et al. 2022

J. Med. Chem.

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“…Promising ways to overcome this problem have recently been reported, but they are still in their infancy and so far not applicable for a broad set of structures . At the moment, a three‐step labeling strategy for [ 18 F]fananserin is described (Scheme ), which depends on a rapid piperazine formation . First, 4‐dinitrobenzene is 18 F‐labeled, then reduced, and condensed with the appropriate naphthosultam derivative to yield 37–100 MBq [ 18 F]fananserin (5–12% overall RCY, non‐decay corrected).…”

Section: Methods Strategies and Difficulties Associated With The Symentioning

confidence: 99%

“…Radiosynthesis of [ 18 F]fananserin (a) Br(CH 2 ) 3 Cl; (b) HN(CH 2 CH 2 OH) 2 , CBr 4 , Ph 3 P; (c) kryptofix 2.2.2., 18 F − , K 2 CO 3 ; (d) Pd/C, H 3 PO 2 ; and (e) NaHCO 3 …”

Section: Methods Strategies and Difficulties Associated With The Symentioning

confidence: 99%

Current radiosynthesis strategies for 5‐HT_2A receptor PET tracers

Herth

Knudsen

2015

Labelled Comp Radiopharmac

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Serotonin 2A receptors have been implicated in various psychophysiological functions and disorders such as depression, Alzheimer's disease, or schizophrenia. Therefore, neuroimaging of this specific receptor is of significant clinical interest, and it is not surprising that many attempts have been made to develop a suitable 5-HT2A R positron emission tomography-tracer. In this review, we give an overview on the precursor, reference compound synthesis, and the preparation of promising 5-HT2A R radiopharmaceuticals applied in positron emission tomography. We also highlight possible learning outcomes that can be made from these tracer development processes.

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“…13 Their condensation with aromatic aldehydes provides compounds with enantiomeric excesses (ee) up to 77%. 14 With the aim of developing new ligands 15 and radioligands 16 for the serotoninergic system and to access to new chiral bases for asymmetric reactions, 17 we have undertaken a search for a reliable synthesis of 3-(Narylamino)pyrrolidines and 3-(N-arylamino)piperidines. Numerous procedures have been reported for the preparation of these compounds including cyclization of amino acids 18 or cyclization of triols and related compounds, 19 reductive amination of pyrrolidinones or piperidinones, 1b,9,10,20 nucleophilic substitution of halides 21 or sulfonates, 3,22 Mitsunobu reaction, 1a and SNAr reactions.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Mediated Arylation of 3-Aminopiperidines and 3-Aminopyrrolidines

et al. 2004

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This paper describes the palladium-catalyzed arylation of 1-substituted 3-aminopyrrolidines or piperidines. Palladium(0) (1-2 mol %) in conjunction with "Buchwald's ligand" [2-(dimethylamino)-2'-(dicyclohexylphosphine)biphenyl] was shown to be the catalyst of choice for the coupling with aryl bromides or chlorides. When bromobenzene was used, a strong temperature effect was noticed. Whereas no reaction occurred at 100 degrees C, yields higher than 85% were obtained at 130 degrees C for each substrate. Such an effect was not observed when diphosphines were used. Whereas Xantphos and, to a lesser extent BINAP, were moderately efficient in the coupling of all diamines, the palladium-mediated arylation in the presence of monophosphines was strongly dependent on the substrate. The results suggest the participation of both nitrogens of the aminoheterocycle in the reactive intermediate. This participation could also account for the highly selective arylation of the endocyclic nitrogen of unsubstituted 3-aminopyrrolidine or piperidine. Optimal conditions were found for the arylation using 2- or 4-substituted electron-poor or enriched aryl halides.

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Preparation of [18F]RP 62203, a selective ligand for the study of serotonin receptors (5-HT2) by rapid “in situ” piperazine formation

Cited by 13 publications

References 18 publications

Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Current radiosynthesis strategies for 5‐HT_2A receptor PET tracers

Palladium-Mediated Arylation of 3-Aminopiperidines and 3-Aminopyrrolidines

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Preparation of [18F]RP 62203, a selective ligand for the study of serotonin receptors (5-HT2) by rapid “in situ” piperazine formation

Cited by 13 publications

References 18 publications

Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors

Current radiosynthesis strategies for 5‐HT2A receptor PET tracers

Palladium-Mediated Arylation of 3-Aminopiperidines and 3-Aminopyrrolidines

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Product

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Current radiosynthesis strategies for 5‐HT_2A receptor PET tracers