Abstract
Multicomponent cyclocondensation of hydrazine derivatives, ethyl acetoacetate, aromatic aldehydes, and 4-hydroxycoumarin has been reported. The optimization details of the developed novel protocol are recorded. The novel procedure features short reaction time, moderate yields, and simple workup. In addition, BMIM[triflate] was chosen as a green solvent. The structures of the obtained benzylpyrazolyl coumarins were determined and confirmed by
1
H NMR,
13
C NMR, IR, and elemental analysis. The MIC values of benzylpyrazolyl coumarin derivatives were determined by the microbroth dilution method using 96-well plates. However, the derivatives
5a
,
5b
,
5d
, and
5g
possess the strongest activities. Compound
5b
was the most active derivative against
Candida albicans
. Moreover, the antioxidant activity determination of these coumarins derivatives
5
(
a
–
g
)–
6
(
a
–
g
) were studied with the DPPH and compared with gallic acid (GA)and butylated hydroxytoluene (BHT). Molecular modelling studies using DFT (density functional theory) calculations showed that there two tautomers
A
and
B
in which
A
is more stable than
B
. The benzylpyrazolyl coumarin derivatives 5e and 6f exhibited the most cytotoxic effect on the promising cytotoxic activity with IC50 values 4.45
μ
g/mL against MDA-MB-231 and 4.85
μ
g/mL against MCF7, respectively.