Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles

Abstract

BackgroundDesign and synthesis of new inhibitor agents to deal with pathogenic microorganisms is expanding. In this project, an efficient, environmentally friendly, economical, rapid and mild procedure was developed for the synthesis of novel functionalized isoxazole derivatives as antimicrobial potentials.MethodsMulticomponent reaction between malononitrile (1), hydroxylamine hydrochloride (2) and different aryl or heteroaryl aldehydes 3a–i afforded novel 5-amino-isoxazole-4-carbonitriles 4a–i in good product yields and short reaction times. Deep eutectic solvent K2CO3/glycerol was used as catalytic reaction media. Structure of all molecules were characterized by different analytical tools. In vitro inhibitory activity of all derivatives was evaluated against a variety of pathogenic bacteria including both Gram-negative and Gram-positive strains as well as some fungi. In addition, their free radical scavenging activities were assessed against DPPH.ResultsBroad-spectrum antimicrobial activities were observed with isoxazoles 4a, b, d. In addition, antioxidant activity of isoxazole 4i was proven on DPPH.ConclusionsIn this project, compounds 4a, b, d could efficiently inhibit the growth of various bacterial and fungal pathogens. Antioxidant properties of derivative 4i were also significant. These biologically active compounds are suitable candidates to synthesize new prodrugs and drugs due to the presence of different functional groups on their rings. Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0488-0) contains supplementary material, which is available to authorized users.

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

“…It is known that isoxazoles and their derivatives exhibit only moderate activity against Pseudomonas aeruginosa and are not active at all against Bacillus subtilis. [ 46–48 ] The starting silatrane 1 , mono‐isoxazole‐linked silatranes 3d‐f and bis‐isoxazole‐linked silatranes 4d‐f were chosen for preliminary screening of antimicrobial activity against bacterial strains of Gram‐positive Enterococcus durans B‐603, Bacillus subtilis B‐407 and Gram‐negative Escherichia coli B‐1238, Pseudomonas aeruginosa RPO1. The results of the antimicrobial activity of the tested silatranes are shown in Table 6.…”

Synthesis and evaluation of antimicrobial and antioxidant activity of novel 7‐Aryl‐6H,7H‐ benzo[f]chromeno[4,3‐b]chromen‐6‐one by MgO nanoparticle as green catalyst

“…Antioxidant activity of derivatives on DPPH was evaluated according to the method of Beyzaei et al In 4 ml of the 0.004% ( w / v ) DPPH methanolic solution, 1 ml of various concentrations (25, 50, 75, and 100 μg/mL) of all derivatives in methanol was added and stand for 30 min at room temperature in darkness. The absorbance was read against blank at 517 nm.…”

Ultrasound-Assisted Synthesis, Antioxidant Activity and Computational Study of 1,3,4-Oxadiazol-2-amines

“…DPPH free radical scavenging activities of prepared 1,3,4-oxadiazoles were evaluated and compared to those of ascorbic acid. 28 1 mL of any oxadiazole at concentrations 25, 50, 75, and 100 µg mL -1 in methanol was added to 4 mL of 0.004% (w/v) methanolic solution of DPPH. The mixed solutions were stored at room temperature for 30 min in darkness.…”