A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Abstract

A series of (1-substituted aryl)-3-(1H-imidazol-1-yl)-1-propanones was synthesized through the N-alkylation of imidazole with 3-dimethylamino-1-(substituted aryl)-1-propanone hydrochlorides (ketonic Mannich bases). A second series of N(1) -substituted imidazoles was obtained by the reduction of the carbonyl function of the imidazole-ketones in the previous series by means of NaBH(4) . All of the compounds were evaluated for antifungal activity against 16 strains of Candida, and 3-(1H-imidazol-1-yl)-1-(4-biphenylyl)-1-propanone emerged as a broad-spectrum antifungal agent. Several 3-(1H-imidazol-1-yl)-1-(2'-(substituted benzyl)oxyphenyl)-1-propanones were also active towards Candida kefyr.

Ball mill and microwave assisted synthetic routes to Fluoxetine

“…Mp = 153-156 °C [lit. Mp = 153-154 °C (Roman et al 2013)]. IR (ATR) 3400 (br), 2946, 2662, 1674, 1334, 1222, 958 cm -1 .…”

Crystal structure of (2E)-2-[1-(4-bromophenyl)-3-(1H-imidazol-1-yl) propylidene]-N-(2,4-dichlorophenyl)hydrazinecarboxamide, C19H16BrCl2N5O

“…A solution of N- (2,4-dichlorophenyl)hydrazinecarboxamide [2] (2.2 g, 10 mmol), 1-(4-bromophenyl)-3-(1H-imidazol-1-yl)-propan-1-one [3] (2.79 g, 10 mmol) and few drops of glacial acetic acid in ethanol (15 mL) was stirred at ambient temperature for 18 h. The reaction mixture was evaporated under reduced pressure and the residue was crystallized from ethanol to give 2.84 g (59%) of the title compound as colourless crystals which were suitable for single crystal x-ray analysis. m.p.…”

(2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile

“…The presence of two carbons linking the azole pharmacophore part and an aromatic residue is a common feature in the available antifungal azoles. Whereas, the reported antifungal candidates bearing a propyl bridige between the aromatic moiety and the azole fragment are limited [8][9][10].…”