Benzodioxan WB

M., Fanelli, F. and De Benedetti, P.G. (1992) Molecular modeling and quantitative structure-activity relationship analysis using theoretical descriptors of 1,4-benzodioxan (WB-4101) related compounds al-adrenergic antagonists. Journal of Molecular Structure (Theochem), 276, 327-340. 

Quaglia, W., Pigini, M., Giannella, M. and Melchiorre, C. (1990) 3-Phenyl analogues of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]-methyl]-l, 4-benzodioxan (WB 4101) as highly selective alpha 1-adrenoceptor antagonists. Journal of Medicinal Chemistry, 33, 2946-2948. 

Nelson, W.L., Powell, M.L., Dyer, D.C., 1979. Absolute configuration of glycerol derivatives 7. Enantiomers of 2-[[[2-(2,6-dimethoxy-phe-noxy)ethyl]amino]methyl]-l,4-benzodioxane (WB 4101), a potent competitive Oi-adrenergic antagonist. J. Med. Chem. 22, 1125-1127. 

Finally, very recently Pallavicini et al., in continuation of a previous study on ortho-monosubstituted compounds, designed and synthesized a series of 2-[(2-phenox-yethyl) aminomethyl]-l,4-benzodioxanes ortho-disubstituted at the phenoxy moiety [99]. The disubstituted analogues were tested for their binding affinities at the three oq-AR subtypes and for the 5-HT1A-R. The affinity values of the new compounds were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known oq-AR antagonist WB-4101 (Scheme 8.1), and of the ortho-monosubstituted derivatives. The results suggested some distinctive aspects in the interaction of the phenoxy moiety of monosubstituted and disubstituted compounds with the cqa-AR and the 5-HTiA receptors. A classical (Hansch) QSAR analysis was applied to the whole... 

Keywords a j-Adrenoreceptor antagonists Quinazoline Benzodioxane moiety Prazosin WB 4101 Cystazosin BMY-7378... 

Benzodioxanes represent one of the oldest and best known classes of a-adrenoreceptor antagonists whose chemical structure incorporates a l,4-benzodioxan-2-yl moiety as the main feature (Melchiorre and Belleau, 1981). WB 4101 (21) is the prototype of a (-adrenoreceptor an-... 

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