In this work, we report the synthesis of some new pyrazole derivatives via an efficient and practical procedure. The structures of the obtained compounds were established using different spectroscopic techniques...
A series of new heterocycle hybrids incorporating pyrazole
and
isoxazoline rings was successfully synthesized, characterized, and
evaluated for their antimicrobial responses. The synthesized compounds
were obtained utilizing N-alkylation and 1,3-dipolar
cycloaddition reactions, as well as their structures were established
through spectroscopic methods and confirmed by mass spectrometry.
To get more light on the regioselective synthesis of new hybrid compounds,
mechanistic studies were performed using DFT calculations with B3LYP/6-31G(d,p)
basis set. Additionally, the results of the preliminary screening
indicate that some of the examined hybrids showed potent antimicrobial
activity, compared to standard drugs. The results confirm that the
antimicrobial activity is strongly dependent on the nature of the
substituents linked pyrazole and isoxazoline rings. Furthermore, molecular
docking studies were conducted to highlight the interaction modes
between the investigated hybrid compounds and the Escherichia
coli and Candida albicans receptors.
Notably, the results demonstrate that the investigated compounds have
strong protein binding affinities. The stability of the formed complexes
by the binding between the hybrid compound 6c, and the
target proteins was also confirmed using a 100 ns molecular dynamics
simulation. Finally, the prediction of ADMET properties suggests that
almost all hybrid compounds possess good pharmacokinetic profiles
and no signs of observed toxicity, except for compounds 6e, 6f, and 6g.
:
Thioaurones are known for more than one hundred years; however, they are relatively less studied. In some way,
due to their appealing as a candidate of photoswitchable molecules, they have led to generating considerable interest in the
last years. In this literature survey, we report and discuss the recent advancements made in the synthesis, reactivity and applications of the thioaurone derivatives. To a great extent, the review summarizes published works from different databases
since 2005.
Quinazolinone and isoxazoline systems have attracted much attention due to their interesting pharmacological properties. The association of these two pharmacophores in a single hybrid structure can boost the biological activity or bring a new one. Inspired by this new paradigm, in the present work we report the synthesis and spectroscopic characterization of new quinazolinone–isoxazoline hybrids. The target compounds were obtained via 1,3-dipolar cycloaddition reactions of arylnitriloxides and N-allylquinazolinone. The synthesized compounds were characterized using spectroscopic techniques such as IR, 1D NMR (1H and 13C), 2D NMR (COSY and HSQC), and high-resolution mass spectrometry (HRMS). The spectral data show that this reaction leads only to the 3,5-disubstituted isoxazoline regioisomer, and that the observed regiochemistry is not affected by the nature of the substituents in the phenyl ring of the dipole. In addition, a theoretical study was performed using density functional theory (DFT) to support the experimental results in regard to the regiochemistry of the studied reactions. The computational mechanistic study was in good agreement with the experimental data.
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