O-Alkylation of 3-Pyridinols.

Nedenskov, Poul; Clauson-Kaas, Niels; Lei, Jørgen; Heide, Henning; Olsen, Gert E.; Jansen, Gert; Lamm, Bo; Samuelsson, Benny

doi:10.3891/acta.chem.scand.23-1791

Cited by 25 publications

(3 citation statements)

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“…*), in a study on some Baclofen analogues, established that the coplanarity of the aromatic ring with the C-3 atom of the GABA chain was necessary for GABAB receptor affinity. Although in the pyridine derivatives 13, 15,16, and 17 such condition is respected, only 16 and 17 show a certain activity.…”

Section: Biological Results and Discussionmentioning

confidence: 99%

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Synthesis and Binding Properties to GABA Receptors of 3‐Hydroxypyridinyl‐ and 3‐Hydroxypiperidinyl‐Analogues of Baclofen

Desideri

Galli

Sestili

et al. 1992

Archiv der Pharmazie

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The synthesis of 3-(3-hydroxy-2-pyridinyl)propanoic acid, 3-(3-hydroxy-2-pyridinyl)-4-aminobutanoic acid, their corresponding piperidine compounds, and of some cyclized derivatives is described. In in vitro assays none of the new compounds shows any noteworthy affinity for GABAA or GABAB receptors; only (R,S)-3-(3-hydroxy-2-pyridinyl)-4-aminobutanoic acid and its lactam inhibited in some degree [3H]GABA binding, at 10(-4) M concentration, with low specificity as regards the two receptors.

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Section: Biological Results and Discussionmentioning

confidence: 99%

“…When the pyridine ring was not reduced, the lactams 13, 15, and 16 wen obtained. Hydrolysis of 16 in alkaline condition, followed by purification on Dowex resin, gave the pyridinyl-GABA analogue 17, as a zwitterion.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Binding Properties to GABA Receptors of 3‐Hydroxypyridinyl‐ and 3‐Hydroxypiperidinyl‐Analogues of Baclofen

Desideri

Galli

Sestili

et al. 1992

Archiv der Pharmazie

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show abstract

“…Moreover, the present catalytic system is compatible with a rather sensitive group such as an allylic ether: 3‐allyloxy‐2‐aminopyridine 12b can be synthesized in 88% yield. It is worth mentioning that the so far only reported approach to 12b – the allylation of the corresponding aminohydroxypyridine – suffers from low yields, very likely as the result of the competing formation of N ‐allyl by‐products 20. Not surprisingly, the presence of the strong electron‐withdrawing nitro group triggers the formation of 2‐amino‐5‐nitropyridine 13b also in absence of Cu(acac) 2 (79% vs. 87% yield).…”

Section: Reactivity Of Various Copper Sources In the Coupling Of 3‐brmentioning

confidence: 99%