Convergent<sup>18</sup>F radiosynthesis: A new dimension for radiolabelling

Li, Lei; Hopkinson, Matthew N.; Yona, Rodrigue Leuma; Béjot, Romain; Gee, Antony D.; Gouverneur, Véronique

doi:10.1039/c0sc00362j

Cited by 37 publications

(25 citation statements)

References 47 publications

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“…Surprisingly, none of the synthesized compounds exhibited any sensible inhibitory activity on PI3Ks. On the other hand, only four compounds (92)(93)(94)(95) were able to potently inhibit STAT5-dependent transcription (Fig. 19).…”

Section: Applications Of Gbbr In Drug Discoverymentioning

confidence: 94%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

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The Groebke-Blackburn-Bienaymé reaction (GBBR) is used for the one-pot synthesis of therapeutically relevant fused imidazoles bridgehead nitrogen heterocyclic compounds from readily available aldehyde, isocyanide and amidine building blocks. The reaction is driven by a wide range of catalysts and can be performed either under solvent or solvent-free conditions, or under microwave irradiation as heat source. The GBBR products can be used for the synthesis of a variety of more complex scaffolds via postmodification reactions. These include cyclization and nucleophilic substitution as well as further MCRs. The GBBR reaction has seen diverse applications in combinatorial and medicinal chemistry and its products are of great use in drug discovery. In this review, we summarize the efforts of the chemistry community in the progress and applications of GBBR since 1998. This review also includes some biological profiles and synthetic scopes of GBBR products. The component variations, postmodifications and secondary transformations will also be discussed throughout this review.

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Section: Applications Of Gbbr In Drug Discoverymentioning

confidence: 94%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

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“…The products 3, 4, and 16, are particularly interesting, as their 18 F analogues are common prosthetic groups [19] used in convergent synthesis [20] of PET probes. Interestingly, we found that the stereocenter in 13 epimerizes in the presence of TBAF (see the Supporting Information).…”

Section: Methodsmentioning

confidence: 99%

Mild Copper‐Catalyzed Fluorination of Alkyl Triflates with Potassium Fluoride

2014

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A chemoselective catalytic fluorination of alkyl triflates is described using potassium fluoride as a fluoride source. Excellent yields of the desired alkyl fluorides are obtained after one hour at 45 °C using 2 mol% of the copper catalyst. With 10 mol% of the catalyst, full conversion can be achieved in less than 10 minutes at 45 °C, and thus makes this procedure potentially suited for the preparation of (18) F-labeled PET probes. As a result of the mild reaction conditions, only the substitution products are observed with no evidence of common side reactions, such as elimination. Reported is a preliminary study of the reaction scope, which demonstrates that the fluorination can be performed in the presence of a wide range of functional groups. Evidence suggests an unusual role of the [IPrCuOTf] catalyst as a phase-transfer catalyst and points to [IPrCuF] as the active fluorinating reagent (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).

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“…Gouverneur und Mitarbeiter zeigten kürzlich, dass 4‐[ 18 F]Fluorbenzaldehyde effiziente Reagentien für die Übertragung von 18 F in klassischen Mehrkomponentenreaktionen sind 14. Insbesondere konnte der 4‐[ 18 F]Fluorbenzaldehyd 14 auf effiziente Weise in Groebke‐Bienaymé‐Blackburn‐Reaktionen eingesetzt werden (Schema ).…”

Section: Methodsunclassified