Abstract
The incidence of fungal infections is a growing serious global health burden. There is an urgent medical demand to acquire new antifungal drug-like compounds having azole nuclei to get rid of the drawbacks of the currently available azole antifungal agents.
The target compounds
were synthesized in a four-step reaction sequence using the appropriate acetophenone derivative as a starting material. The antifungal potential of the title compounds was assessed using DIZ and MIC assays according to the reported standard procedures.
The newly synthesized oximino esters
were identified with the aid of various spectroscopic approaches. Their assigned chemical structures were confirmed via single-crystal X-ray structure of compound
. The molecular structure of compound
was crystallized in the triclinic,
-1,
=9.898 (3) Å,
=10.433 (3) Å,
=11.677 (4) Å,
=86.886 (6)°,
=87.071 (7)°,
=64.385 (6)°,
=1,085.2 (6) Å3,
=2. The synthesized compounds
were in vitro evaluated for antifungal potential against four fungal strains. Compounds
and
bearing a trifluoromethylphenyl moiety showed the best anti-
activity with minimum inhibitory concentration (MIC) value of 0.148 μmol/mL, while compound
displayed the best activity toward
with MIC value of 0.289 μmol/mL. Compounds
and
were the most active congeners against Candida parapsilosis and
, respectively.
Single-crystal X-ray analysis of compound
confirmed without doubt the assigned chemical structures of the title compounds as well as confirmed the (
)-configuration of their oximino group. Compounds
and
emerged as the most active compounds against the tested fungi and they could be considered as new antifungal lead candidates.