Synthesis of [4,6‐<sup>3</sup>H]‐2‐pyridone and [<sup>3</sup>H]‐RS‐91309

Keczer, Steve de; Pames, Howard

doi:10.1002/jlcr.2580360808

Cited by 4 publications

(1 citation statement)

References 2 publications

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“…Pharmacologically meaningful binding of openers has been described using the tritiated pinacidil analogue, [ 3 H]-P1075 (Bray & Quast, 1992;Manley et al, 1993;Quast et al, 1993). However, little has been forthcoming from benzopyran (cromakalim)-type radioligands, although (preliminary) reports on such compounds have appeared (Howlett & Longman, 1992;De Keczer & Parnes, 1995). It was therefore of interest to synthesise a potent tritiated ligand belonging to the benzopyran class of openers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure

Manley

Löffler-Walz

Russ

et al. 2001

British J Pharmacology

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The synthesis of a tritiated benzopyran‐type opener of the ATP‐dependent K+ channel (KATP channel), [3H]‐PKF217 – 744 {(3S,4R)‐N‐[3,4‐dihydro‐2,2‐dimethyl‐3‐hydroxy‐6‐(2‐methyl‐4‐pyridinyl)‐2H‐1‐benzopyran‐4‐yl]‐3‐[2,6‐3H]pyridinecarboxamide} with a specific activity of 50 Ci mmol−1 is described. Binding of the ligand was studied in membranes from human embryonic kidney cells transfected with the sulphonylurea receptor isoforms, SUR2B and SUR2A, respectively. PKF217 – 744 was confirmed as being a KATP channel opener by its ability to open the Kir6.1/SUR2B channel, the recombinant form of the vascular KATP channel, and to inhibit binding of the pinacidil analogue, [3H]‐P1075, to SUR2B (Ki=26 nM). The kinetics of [3H]‐PKF217 – 744 binding to SUR2B was described by rate constants of association and dissociation of 6.9×106 M−1 min−1 and 0.09 min−1, respectively. Binding of [3H]‐PKF217 – 744 to SUR2B/2A was activated by MgATP (EC50∼3 μM) and inhibited (SUR2B) or enhanced (SUR2A) by MgADP. Binding of [3H]‐PKF217 – 744 to SUR2B was inhibited by representatives of the different structural classes of openers and sulphonylureas. Ki values were identical with those obtained using the opener [3H]‐P1075 as the radioligand. Glibenclamide accelerated dissociation of the SUR2B‐[3H]‐PKF217 – 744 complex. The data show that the affinity of [3H]‐PKF217 – 744 binding to SUR2B is ∼6 times lower than that of [3H]‐P1075. This is due to a surprisingly slow association rate of the benzopyran‐type ligand, suggesting a complex mechanism of opener binding to SUR. The other pharmacological properties of the two opener radioligands are identical. British Journal of Pharmacology (2001) 133, 275–285; doi:10.1038/sj.bjp.0704071

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure

Manley

Löffler-Walz

Russ

et al. 2001

British J Pharmacology

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Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki–Miyaura Coupling of 3,5‐ and 4,6‐Dibromo‐2‐tosyloxypyridines

Park

Kwon

et al. 2017

Adv Synth Catal

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ChemoselectiveS uzuki-Miyaura reactions on 3,5-and4 ,6-dibromo-2-tosyloxypyridines have been studied for the preparation of trisubstituted pyridines.T he optimized conditions allow for af acile access to 3,5-and 4,6-diaryl-2-tosyloxypyridines in yields of 8t o99%. Further functionalization such as palladium-catalyzed amination andc opper-free Sonogashira reactionofthe tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesiso fn ovel and biologically relevant tri-substituted pyridines.T he formal synthesis of ficuseptine,abioactive alkaloid, hasa lso been achieved via the palladium-catalyzed cross-coupling reaction of 3,5-dibromo-2-tosyloxypyridinei n5steps from 3,5-dibromo-2-hydroxypyridine with 50% overall yield.

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Dehydrogenative Oxidation of Alcohols by Reusable Iridium Catalysts with a Cooperative Polymer Ligand

Maeda,

Kuno,

Jeong

et al. 2024

ChemCatChem

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A series of iridium‐polymer complexes containing bipyridonate moieties were synthesized. The high catalytic performance of the iridium‐polymer complex for the dehydrogenative oxidation of alcohols was demonstrated. Notably, the bipyridonate moiety in the polymer structure acts as a chemically non‐innocent "functional ligand", realizing the enhancement of dehydrogenation process. While numerous metal‐polymer catalysts have been reported so far, to our knowledge, introducing a "functional ligand" into a polymer chain that can operate cooperatively with transition metals by changing their structures during the catalytic processes is rare. The iridium‐polymer complex could be easily separated from the product and recovered by precipitation upon the addition of methanol after the catalytic reaction. Furthermore, the recovered catalyst could be reused without loss of catalytic efficiency at least ten times.

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Synthesis of [4,6‐³H]‐2‐pyridone and [³H]‐RS‐91309

Cited by 4 publications

References 2 publications

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki–Miyaura Coupling of 3,5‐ and 4,6‐Dibromo‐2‐tosyloxypyridines

Dehydrogenative Oxidation of Alcohols by Reusable Iridium Catalysts with a Cooperative Polymer Ligand

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Synthesis of [4,6‐3H]‐2‐pyridone and [3H]‐RS‐91309

Cited by 4 publications

References 2 publications

Synthesis and characterization of a novel tritiated KATP channel opener with a benzopyran structure

Synthesis and characterization of a novel tritiated KATP channel opener with a benzopyran structure

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki–Miyaura Coupling of 3,5‐ and 4,6‐Dibromo‐2‐tosyloxypyridines

Dehydrogenative Oxidation of Alcohols by Reusable Iridium Catalysts with a Cooperative Polymer Ligand

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Synthesis of [4,6‐³H]‐2‐pyridone and [³H]‐RS‐91309

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure

Synthesis and characterization of a novel tritiated K_ATP channel opener with a benzopyran structure