Unusual transformation of the 3-hydroxy-picolinoyl residue of pristinamycin IA.
Pristinamycin IA was modified in a two-step procedure to give original derivatives possessing a tricyclic nucleus (8a, 8b, 8c) or a substituted pyrrole ring (10a, 10b) in place of the natural exocyclic 3-hydroxy-picolinoyl residue. This transformation involved firstly preparation of pyridinium betaines 5 from pristinamycin IA and secondly a 1-3 dipolar cycloaddition between 5 and N-substituted maleimides or diethyl acetylenedicarboxylate. The compounds obtained were evaluated as antibacterial agents alone and in association with pristinamycin IIA.
Paris
J M
JM
Rhône-Poulenc Rorer S.A., Centre de Recherche de Vitry-Alfortville, Vitry sur Seine, France.
Francois
J
J
Molherat
C
C
Albano
F
F
Robin
M
M
Vuilhorgne
M
M
Barriere
J C
JC
D000478:Alkylation; D001622:Betaine / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D010847:Picolines / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D014769:Virginiamycin / Q000031:analogs & derivatives / Q000737:chemistry*
D010847:Picolines; D011758:Pyrroles; D014769:Virginiamycin; D001622:Betaine