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α 1 ‐ and α 2 ‐Adrenoreceptor Antagonist Profiles of 1‐ and 2‐[ ω ‐(4‐Arylpiperazin‐1‐yl)alkyl]‐1,2,3‐benzotriazoles
Author(s) -
Boido Alessandro,
Budriesi Roberta,
Boido Caterina Canu,
Ioan Pierfranco,
Terranova Emanuela,
Chiarini Alberto,
Sparatore Fabio
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590100
Subject(s) - chemistry , alkyl , antagonist , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , receptor
A series of pharmacologically interesting 1‐ and 2‐[ ω ‐(4‐arylpiperazin‐1‐yl)alkyl]‐1,2,3‐benzotriazoles, compounds 1 – 27 , were synthesized ( Scheme ) and subjected to various biological studies to identify structure–activity relationships (SAR). The new compounds were found to exhibit good non‐selective binding affinity towards the α 1 ‐adrenoreceptor ( Table 1 ). In several cases, high functional antagonism was observed towards the α 1A ‐, α 1B ‐, and α 1D ‐adrenoreceptor subtypes ( Table 2 ). The selectivity for these three subtypes was comparable with or superior to that displayed by the standard drug prazosin. The most‐common selectivity rank order was α 1D > α 1B > α 1A , followed by α 1B > α 1D > α 1A . In functional experiments, antagonism towards the α 2 ‐adrenoreceptor was generally low; however, a few compounds were endowed with significant antagonist properties (p A 2 values of up to 7.87).