SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF N EW UREIDO AND DICARBONIC ACID DIAMIDO DERIVATIVES OF ACYLPENICILLINES WITH AND WITHOUT CATECHOL SUBSTITUENTS

New ureido, oxamoyl, fumaramoyl and terephthalamoyl derivatives of amp icillin or amoxicillin were synthesized by reaction of acylpenicilline s with o-dihydroxy- or o-diacyloxy substituents containing aromatic am ines bound over CO- or dicarboxylic groups. Corresponding compounds de rived from 3,4-diacetoxyaniline showed significant increase of activit y against pseudomonas and salmonella in contrast to derivatives withou t catechol substituents. No increase of activity was observed by corre sponding derivatives of bi- and tricyclic amines. Derivatives with oxa moyl, fumaramoyl or terephthalamoyl groups were found to be more activ e than the corresponding ureido derivatives. Studies with mutants poss essing higher membrane permeability have shown that the high activitie s of catechol containing derivatives are connected with the improved p enetration through the outer membrane. Some new penicillin derivatives are more stable against beta-lactamases compared with azlocillin.