Synthesis, antimicrobial, antioxidant and docking study of novel isoxazoline derivatives

Abstract

INTRODUCTIONSynthesis and evaluation of efficacious antimicrobial, due to limited number of effective drugs 1 and antioxidant agents to protect human body from free radicals 2 represent the main goal for the several research groups worldwide. Recently, considerable attention has been given to isoxazoline derivatives due to their varied pharmacological activities like antimicrobial 3 , anti-inflammatory 4 , anti-tubercular 5 , antidepressant 6 , antioxidant 7 , antitumor and DNA Methyltransferase 1 Inhibitors 8 . Therefore, our attempts to find novel antimicrobial and antioxidant agents focus on the isoxazoline derivative. A novel series of isoxazolines (3-10) were synthesized and characterized by spectral data. Isoxazoline derivatives (3-ABSTRACT A novel series of isoxazoline derivatives (3-10) was synthesized and characterized by using spectral analysis. The synthesized derivatives were in vitro screened against several bacterial species as well as Candida albicans and exhibit moderate to potent activity. All the synthesized products were screened qualitatively for their antioxidant property by using TLC technique and the percent DPPH radical scavenging activity of the potent derivatives (4-6,8) were evaluated. Docking study of isoxazoline derivatives 7 and 8 against L-Glutamine: D-fructose-6-phosphate amidotransferase (glucosamine-6-phosphate synthase), the target enzyme in antimicrobial chemotherapy, was evaluated to explore the interactions of the synthesized hits inside the amino acid residues of the enzyme active site. The docking outcomes strongly supported the in vitro assay of new derivatives against several microbial species.

Synthesis, Antibacterial Activity, and Molecular Docking Study of Bispyrazole‐Based Derivatives as Potential Antibacterial Agents

“…[,35] Claisen‐Schmidt condensation was used for the synthesis of compound 5 (80 %) from equimolar starting materials including 3‐(4‐bromophenyl)‐1‐phenyl‐1 H ‐pyrazole‐4‐carbaldehyde 4 and p ‐methoxyacetophenone by using as a base, sodium hydroxide (NaOH) and ethanol is used as a solvent. followed by a dehydration reaction [36] . Using a cyclocondensation reaction of phenyl hydrazine chalcone 5 in absolute ethanol with a few drops of glacial acetic acid under reflux, bispyrazole 6 was synthesized (yield 78 %) [37] .…”

“…followed by a dehydration reaction. [36] Using a cyclocondensation reaction of phenyl hydrazine chalcone 5 in absolute ethanol with a few drops of glacial acetic acid under reflux, bispyrazole 6 was synthesized (yield 78 %). [37] Aromatization reaction involving Suzuki cross coupling reaction [38][39][40][41][42] has applied for the synthesis of bispyrazole derivatives (8 a-h) with a yield ranging from 68 to 83 %.…”

New Pyrazoline Derivatives Containing Imine Moiety: Synthesis, Characterization and Antimicrobial Study

“…These compounds were synthesized according to the modified method described in the reported references [13] .To a solution of aromatic aldehydes (1mmol) was dissolved in ethanol absolute (20 ml) containing few drops of glacial acetic acid and then the pyrazoline derivative (2) (1mmol) was added. The mixture was refluxed for (10-12 hrs) and the reaction process was monitored by TLC using Hexane: Ethylactate (1:4) as an eluent.…”

Synthesis, Antimicrobial, Antioxidant and Docking Study of Novel 2H-1,4-Benzoxazin-3(4H)-One Derivatives

“…DPPH has absorption at 517 nm which disappears when DPPH is reduced by an antioxidant compound or a radical species to become a stable diamagnetic molecule. As a result, the color changes from purple to yellow [21]. This change in color is taken as an indicator of the ability of hydrogen to donate to tested compounds.…”