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.
|Titolo:||Synthesis and antimicrobial activity of arylazoenamines|
|Autori interni:||SPARATORE, ANNA CONCETTINA|
|Parole Chiave:||Spectrophotometry, Infrared; Mass Spectrometry; Bacteria; Anti-Infective Agents; Anti-Bacterial Agents; X-Ray Diffraction; Fungi; Spectrophotometry, Ultraviolet; Candida; Microbial Sensitivity Tests; Azo Compounds; Magnetic Resonance Spectroscopy|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||giu-1993|
|Appare nelle tipologie:||01 - Articolo su periodico|