1-Aryl-3-(1H-imidazol-1-yl)propan-1-ol esters: synthesis, anti-Candida potential and molecular modeling studies.

Background: An increased incidence of fungal infections, both invasive and superficial, has been witnessed over the last two decades. Candida species seem to be the main etiology of nosocomial fungal infections worldwide with Candida albicans, which is commensal in healthy individuals, accounting for the majority of invasive Candida infections with about 30-40% of mortality.

Results: New aromatic and heterocyclic esters 5a-k of 1-aryl-3-(1H-imidazol-1-yl)propan-1-ols 4a-d were successfully synthesized and evaluated for their anti-Candida potential.

In vitro anti-Candida activity of certain new 3-(1H-imidazol-1-yl)propan-1-one oxime esters.

Anti-Candida activities of certain new oximes 4a-d and their respective aromatic esters 5a-l are reported. The tested compounds 4a-d and 5a-l exhibited better anti-Candida profiles than fluconazole. Compound 5j, namely (E)-3-(1H-imidazol-1-yl)-1-phenylpropan-1-one O-4-chlorobenzoyl oxime emerged as the most active congener, with a MIC value of 0.

(E)-N-[3-(Imidazol-1-yl)-1-phenyl-propyl-idene]hydroxyl-amine.

The title compound, C(12)H(13)N(3)O, exists in an E configuration with respect to the C=N bond [1.285 (2) Å]. The imidazole ring forms a dihedral angle of 75.