ANTIBIOTIC X-5108 .9. CHEMICAL CONVERSION OF MOCIMYCIN TO AURODOX AND DERIVATIVES OF AURODOX, GOLDINAMINE AND MOCIMYCIN

Mocimycin was converted to the acylesters by selective acylation of the hydroxyl group of the 4-hydroxy-l-methyl-2(lH)pyridinone moiety. Subsequent N-methylation at the nuclear nitrogen and removal of the protective group from the resulting reaction products afforded aurodox. Mono-O-acetylmocimycin and several analogous aurodox esters thus prepared possess antibacterial activity in vitro and growth-promotion properties in poultry.Esters of aurodox involving the hydroxyl group of the 4-hydroxy-1-methy1-2(lH)pyridinone moiety are activated. Accordingly, acetic acid treatment of the aurodox esters generates O-acylgoldinamines which undergo transacylation furnishing N-acylgoldinamines. Alternatively, N-acylgoldinamines can be prepared by selective mono-O-arylsulfonylation of aurodox, liberating O-arylsulfonylgoldinamine by treatment with acetic acid followed by N-acylation and removal of the protective arylsulfonyl group. A third approach to N-acylgoldinamines consists in direct N-acylation of goldinamine itself which is prepared by acetic acid treatment of aurodox. None of these derivatives prepared, however, exhibited significant antimicrobial or growth-promoting properties, suggesting that the goldinonic acid moiety, or a closely related derivative thereof, is required for biological activity. © 1979, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.