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Synthesis and antimicrobial activity of arylazoenamines

Canu Boido, C.; Boido, V.; Sparatore, F.; Sparatore, A.; Bombieri, G.; Benetollo, F.; Debbia, E.; Pesce Schito, A.

Farmaco 48(6): 749-775

1993

ISSN/ISBN: 0014-827X
PMID: 8373502
Document Number: 408120
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.

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