title: Cage dimeric N-acyl- and N-acyloxy-4-aryl-1,4-dihydropyridines as first representatives of a novel class of HIV-1 protease inhibitors.
abstract: The synthesis of a series of novel cage dimeric N-acyl and N-acyloxy-4-aryl-1,4-dihydropyridines starting either from solid-state synthetic ester dimers or from monomeric 4-aryl-1,4-dihydropyridines is presented. Their biological evaluation as novel HIV-1 protease inhibitors showed the most active compounds to be 5c and 5i with inhibitory activities of 52% (50 microM) and 49% (25 microM), respectively. Within each series of N-acyl- and N-acyloxy derivatives NCOBz and NBoc groups were found to be the best substituents. Although they exhibiting only moderate activities these cage dimers hold promise as a class of novel non-peptidic HIV-1 protease inhibitors.
authors.affiliation: Institut für Pharmazeutische Chemie der Martin-Luther-Universität Halle-Wittenberg, Germany.
authors.forename: A
authors.initials: A
authors.lastname: Hilgeroth
authors.forename: A
authors.initials: A
authors.lastname: Billich
mesh_terms: D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D019258:Saquinavir / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D004095:Dihydropyridines; D017320:HIV Protease Inhibitors; D019258:Saquinavir