Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET

Langer, Oliver; Dollé, Frédéric; Loc’h, Christian; Halldin, Christer; Vaufrey, Françoise; Coulon, Christine; Crouzel, C.; Någren, Kjell; Mazièré, B.

doi:10.1002/(sici)1099-1344(199710)39:10<803::aid-jlcr27>3.0.co;2-r

Cited by 8 publications

(1 citation statement)

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“…Hypobromous acid and related sources of "positive bromine" can introduce a substituent adjacent to bulky groups in an aromatic ring (40). Trifluoroacetyl hypobromite (CF 3 -COOBr), a relative of HOBr, also produced different electrophilic substituted products from those of Br 2 on phenol analogues (41). Unified Consideration of the Nature and Activity of the Bromination Reagent and the Reactivity of the Substrate.…”

Section: Resultsmentioning

confidence: 99%

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

et al. 2009

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No-carrier-added (NCA) 76Br labeling of 4-(5-Acetoxy-7-bromobenzoxazol-2-yl)phenyl acetate, a diacetate-protected estrogen-receptor beta (ERβ) selective ligand, was carried out successfully using [76Br]bromide ion. The labeling was achieved via oxidative electrophilic destannylation of an organotin precursor molecule by modification of the leaving group (from Bu3Sn to Me3Sn) and the addition of methanol to the reaction mixture. The differences between the oxidative bromination reaction under small-scale macroscopic vs tracer level radiochemical conditions were explored in terms of effective brominating agents, which depend greatly on the nature of the solvent during the radiochemical bromination, and the potential interference by trace levels of highly reactive impurities in the reaction that compete for the desired bromination at the NCA level. Our observations, and our development of experimental protocols for successful radiobromination at the tracer NCA-scale, should be applicable to the synthesis of other radiobromine-labeled organic compounds of potential interest as PET radiopharmaceuticals and radiotherapy agents.

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Section: Resultsmentioning

confidence: 99%

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

et al. 2009

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The sequential syntheses of [⁷⁶Br]FBAU 3′,5′‐dibenzoate and [⁷⁶Br]FBAU

Kao

Sassaman

Szajek

et al. 2001

Labelled Comp Radiopharmac

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Radiohalogen incorporation into organic systems

Bolton

2002

Labelled Comp Radiopharmac

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SummaryThis Review reports the more recent applications of radiohalogen labelling in organic compounds. Modern synthetic methods place more emphasis upon substitution at specific sites. Electrophilic substitution, especially at aromatic carbon atoms, involves displacement of halogen or of metals rather than the earlier popular halogen-deprotiation processes. Nucleophilic displacement, at either aliphatic or aromatic sites, has also become widespread since it may be made more selective by the inclusion of appropriate activating groups or suitable displaced groups. Microwave and thermally induced methods are both reported with a critical assessment of the value of each process.

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Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET

Cited by 8 publications

References 8 publications

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

The sequential syntheses of [⁷⁶Br]FBAU 3′,5′‐dibenzoate and [⁷⁶Br]FBAU

Radiohalogen incorporation into organic systems

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Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET

Cited by 8 publications

References 8 publications

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: 76Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: 76Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

The sequential syntheses of [76Br]FBAU 3′,5′‐dibenzoate and [76Br]FBAU

Radiohalogen incorporation into organic systems

Contact Info

Product

Resources

About

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

Bromination from the Macroscopic Level to the Tracer Radiochemical Level: ⁷⁶Br Radiolabeling of Aromatic Compounds via Electrophilic Substitution

The sequential syntheses of [⁷⁶Br]FBAU 3′,5′‐dibenzoate and [⁷⁶Br]FBAU