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Novel tricyclic Delta(2)-isoxazoline and 3-oxo-2-methyl-isoxazolidine derivatives: synthesis and binding affinity at neuronal nicotinic acetylcholine receptor subtypes.

Abstract：

:A group of novel tricyclic Delta(2)-isoxazolines (4b, 5b, 7a-b, and 8a-b) and 3-oxo-isoxazolidines (6a-b and 9a-b), structurally related to cytisine or norferruginine, was prepared through 1,3-dipolar cycloadditions involving suitable olefins and bromonitrile oxide. The target compounds were assayed at alpha4beta2 and alpha7 neuronal acetylcholine receptors (nAChRs). The results of competition binding experiments indicated for the new derivatives a reduction of the affinity at the alpha4beta2 subtype in comparison with the reference molecules, coupled with an overall negligible affinity at the alpha7 subtype. The binding mode of the bromo-Delta(2)-isoxazolines 4b and 7b, which were the highest affinity ligands in the series (K(i)=0.92 and 0.75 microM, respectively), was analyzed by applying a recently developed model of the alpha4beta2 nAChRs.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Dallanoce C,Frigerio F,Martelli G,Grazioso G,Matera C,Pomè DY,Pucci L,Clementi F,Gotti C,De Amici M

doi

10.1016/j.bmc.2010.04.065

subject

Has Abstract

pub_date

2010-06-15 00:00:00

pages

4498-508

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00377-9

journal_volume

18

pub_type

杂志文章

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