Antifungal activity of novel 5-carbonyl derivatives of 3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines.
The synthesis and antifungal activity of a series of novel 5-carbonyl derivatives of 3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines (4) are discussed. The preparation of the title compounds involved a 1,3-dipolar cycloaddition reaction of alpha-substituted ketonitrones with either acrylic esters, acrylamide or methyl vinyl ketone to furnish cis/trans-diastereomeric mixtures of the desired 5-carbonyl isoxazolidines 4. The anifungal activity was evaluated in vitro in solid agar cultures. Some of the compounds tested exerted moderate to potent activity against a wide variety of dermatophytes and yeast and systemic fungi.
Bennett
G A
GA
Mullen
G B
GB
DeCory
T R
TR
Maryniak
D M
DM
Jones
W E
WE
Mitchell
J T
JT
Allen
S D
SD
St Georgiev
V
V
D000935:Antifungal Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005658:Fungi / Q000187:drug effects; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010080:Oxazoles / Q000138:chemical synthesis*
D000935:Antifungal Agents; D007093:Imidazoles; D007555:Isoxazoles; D010080:Oxazoles