Synthesis and antimicrobial activity of arylazoenamines.
The possibility to obtain new arylazoenamines endowed with antifungal activity was examined by reacting with acids the arylhydrazones of several keto- and aldo-tert, amines as dimethyl-3-aminoacetone, 3-quinuclidinone, 1-methyl-3-piperidone and 2-formyl-1-methylpyrrolidine. The reaction was successful only in the last two cases. From each 1-methyl-3-piperidone arylhydrazone two isomeric arylazoenamines were formed, which were identical with those obtained from the analogous arylhydrazone of 2-formyl-1-methylpyrrolidine. The structure of these compounds was settled on the ground of UV, IR, NMR and mass spectra and confirmed by means of X-ray analysis. A mechanism is proposed for the formation of arylazoenamines through the contraction of piperidine ring and enlargement of the pyrrolidinic one. The prepared compounds [3-arylazo-1-methyl-delta 2-piperideines 17 and 1-methyl-2(arylazo)methylene pyrrolidines 18 exhibited only a very weak antibacterial activity, but were moderately active against several Candida species and other yeast-like fungi.
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
C
C
Canu Boido
V
V
Boido
F
F
Sparatore
A
A
Sparatore
G
G
Bombieri
F
F
Benetollo
E
E
Debbia
A
A
Pesce Schito
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D001391:Azo Compounds