The optical isomers of the well known alpha(1) - antagonist WB4101 and of its derivatives with a methyl group in the oxyethyl moiety were prepared for the evaluation of their alpha - adrenoceptors binding affinity. By means of a detailed computational analysis, the present work shows that the introduction of a methyl group affects the behaviour of WB4101 in different ways. A limitation of the conformational freedom in certain regions of the torsional subspace of the potential energy function, differences in the reactivity of the protonated species towards a model proton acceptor and the quality of the superposition with the rigid template for alpha(1) antagonists, corynanthine, are examined and discussed in order to select a candidate bioactive form and possible features which act as modulators of the recognition process at the the alpha(1) - adrenoceptors.

The optical isomers of the well known α1-antagonist WB4101 and of its derivatives with a methyl group in the oxyethyl moiety were prepared for the evaluation of their α-adrenoceptors binding affinity. By means of a detailed computational analysis, the present work shows that the introduction of a methyl group affects the behaviour of WB4101 in different ways. A limitation of the conformational freedom in certain regions of the torsional subspace of the potential energy function, differences in the reactivity of the protonated species towards a model proton acceptor and the quality of the superposition with the rigid template for α1 antagonists, corynanthine, are examined and discussed in order to select a candidate bioactive form and possible features which act as modulators of the recognition process at the α1-adrenoceptors.

Molecular properties of the WB4101 enantiomers and of its chiral methyl derivatives for α1-adrenoceptor recognition / Villa, L.; Valoti, E.; Villa, A. M.; Pallavicini, M.; Ferri, V.; Iuliano, E.; Brunello, N.. - In: IL FARMACO. - ISSN 0014-827X. - 49:9(1994), pp. 587-606.

Molecular properties of the WB4101 enantiomers and of its chiral methyl derivatives for α1-adrenoceptor recognition

Brunello N.
1994

Abstract

The optical isomers of the well known α1-antagonist WB4101 and of its derivatives with a methyl group in the oxyethyl moiety were prepared for the evaluation of their α-adrenoceptors binding affinity. By means of a detailed computational analysis, the present work shows that the introduction of a methyl group affects the behaviour of WB4101 in different ways. A limitation of the conformational freedom in certain regions of the torsional subspace of the potential energy function, differences in the reactivity of the protonated species towards a model proton acceptor and the quality of the superposition with the rigid template for α1 antagonists, corynanthine, are examined and discussed in order to select a candidate bioactive form and possible features which act as modulators of the recognition process at the α1-adrenoceptors.
1994
49
9
587
606
Molecular properties of the WB4101 enantiomers and of its chiral methyl derivatives for α1-adrenoceptor recognition / Villa, L.; Valoti, E.; Villa, A. M.; Pallavicini, M.; Ferri, V.; Iuliano, E.; Brunello, N.. - In: IL FARMACO. - ISSN 0014-827X. - 49:9(1994), pp. 587-606.
Villa, L.; Valoti, E.; Villa, A. M.; Pallavicini, M.; Ferri, V.; Iuliano, E.; Brunello, N.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1247736
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