Synthesis and .beta.-adrenoceptor activity of the erythro and threo isomers of substituted .alpha.-hydroxytrimetoquinol
| Autor: | Dennis R. Feller, Peter Osei-Gyimah, Michael T. Piascik, Duane D. Miller, John W. Fowble |
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| Rok vydání: | 1978 |
| Předmět: |
Male
Magnetic Resonance Spectroscopy Stereochemistry Guinea Pigs Stereoisomerism In Vitro Techniques Guinea pig chemistry.chemical_compound Heart Rate Adipocyte Drug Discovery Cyclic AMP Animals Lipolysis Chemistry Airway Resistance Diastereomer Biological activity Nuclear magnetic resonance spectroscopy Adrenergic beta-Agonists Isoquinolines Lipid Metabolism Rats Adipose Tissue Molecular Medicine Female Tretoquinol Cyclase activity |
| Zdroj: | Journal of Medicinal Chemistry. 21:1173-1178 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00209a019 |
| Popis: | The synthesis and pharmacological activity of erythro and threo isomers of 1-(3',4',5'-trimethoxy-alpha-hydroxy-benzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, 2 and 3, are reported. The structural assignments of 2 and 3 are based upon NMR spectra of the 6,7-dibenzyl precursors, 6 and 10, and of the synthetic derivatives of 13alpha- and 13beta-hydroxy-2,3-(dibenzyloxy)-9,10,11-trimethoxytetrahydroprotoberberine, 8 and 12, respectively. The erythro isomer 2 was a more potent beta-adrenoceptor stimulant than the threo isomer 3 in guinea pig atrial, guinea pig tracheal, and rat adipocyte preparations. The differential activity of these compounds on lipolysis was favorably correlated to changes in the stimulation of adenylate cyclase activity and cAMP accumulation in rat adipocytes. |
| Databáze: | OpenAIRE |
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