Synthesis of N-substituted isocyanocarboxamides with antimicrobial activity.
The Ugi four-component condensation between isocyanides 1, cycloketones 2, and ammonium formate affords N-substituted formylaminocarboxamides 3 which are dehydrated with POCl3/NEt3 to give the title compounds 4. The structure of the compounds 3 and 4 was confirmed by spectral data and elemental analyses. In vitro tests of antibacterial activity showed that compounds 4 are ineffective against E. coli and fairly active against K. pneumoniae, B. subtilis and S. aureus. A very good antimicotic activity was shown against C. albicans.
Bossio
R
R
Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, Italy.
Marcaccini
S
S
Pepino
R
R
Pellegrini
G
G
Polsinelli
M
M
D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000577:Amides; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D009570:Nitriles