Butyrophenones and Diphenylbutylpiperidines

Janßen, Paul

doi:10.1016/b978-0-12-290558-2.50012-5

Cited by 6 publications

(1 citation statement)

References 211 publications

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“…Butyrophenones are tertiary amines derived from 4-aminobutyrophenone, of which most important structural features associated with their high neuroleptic potency are an unbranched propylene side chain, a fluoro substituent in position 4', and a second benzene ring directly or indirectly linked to position 4 of a basic six-membered ring (Janssen, 1974). These structural features give butyrophenones a high hydrophobicity, which is reflected in their respective logP values (ranged between 1.84 and 6.98 for the studied compounds).…”

Section: Resultsmentioning

confidence: 99%

Development of predictive retention–activity models of butyrophenones by biopartitioning micellar chromatography

Martı́n-Biosca

Molero-Monfort

Sagrado

et al. 2001

Biomedical Chromatography

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The predictive and interpretative capability of quantitative chromatographic retention-biological activity models is supported by the fact that in adequate experimental conditions the solute partitioning into the chromatographic system can emulate the solute partitioning into lipid bilayers of biological membranes, which is the basis of drug and metabolite uptake, passive transport across membranes and bioaccumulation. The use of retention data obtained in biopartitioning micellar chromatography (BMC) has been demonstrated to be helpful in describing the biological behaviour of different kinds of drugs. In this chromatographic system, polioxyethylene 23 lauryl ether Brij35 micellar mobile phases and C 18 reversed stationary phase in adequate experimental conditions are used. The RP-HPLC capacity factors of butyrophenones were determined using different Brij35 concentrations as micellar mobile phases. Relationships between seven biological activities of butyrophenones reported in bibliography and retention data were established and their predictive and interpretative ability evaluated. These relationships were significant between preclinical pharmacology and therapeutic efficacy parameters and the retention factors of butyrophenones (0.89 < R 2 < 0.98). The results indicate that the retention of compounds in BMC is capable of describing and predicting in vitro the biological activities of butyrophenones. This approach can be very useful in the development of new neuroleptic drugs, avoiding the use of experimental animals.

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Section: Resultsmentioning

confidence: 99%