Dataset Information

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

ABSTRACT:

Background

Design 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.

Methods

Multicomponent 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.

Results

Broad-spectrum antimicrobial activities were observed with isoxazoles 4a, b, d. In addition, antioxidant activity of isoxazole 4i was proven on DPPH.

Conclusions

In 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.

SUBMITTER: Beyzaei H

PROVIDER: S-EPMC6768021 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Publications

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

Beyzaei Hamid H Kamali Deljoo Mahboubeh M Aryan Reza R Ghasemi Behzad B Zahedi Mohammad Mehdi MM Moghaddam-Manesh Mohammadreza M

Chemistry Central journal 20181115 1

<h4>Background</h4>Design 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.<h4>Methods</h4>Multicomponent reaction between malononitrile (1), hydroxylamine hydrochloride (2) and different aryl or heteroaryl aldehydes 3a-i afforded novel 5-amino-isoxazole-4-c ...[more]

PMID: 30443685

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Project description:The aim of the experiment was a green synthesis of cobalt nanoparticles from the aqueous extract of Ziziphora clinopodioides Lam (CoNPs) and assessment of their cytotoxicity, antioxidant, antifungal, antibacterial, and cutaneous wound healing properties. The synthesized CoNPs were characterized using different techniques including UV-Vis., FT-IR spectroscopy, X-ray diffraction (XRD), energy dispersive X-ray spectrometry (EDS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). According to the XRD analysis, 28.19 nm was measured for the crystal size of NPs. TEM and SEM images exhibited a uniform spherical morphology and average diameters of 29.08 nm for the biosynthesized nanoparticles. Agar diffusion tests were done to determine the antibacterial and antifungal characteristics. Minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) were specified by macro-broth dilution assay. CoNPs indicated higher antibacterial and antifungal effects than many standard antibiotics (p???0.01). Also, CoNPs prevented the growth of all bacteria at 2-4 mg/mL concentrations and removed them at 2-8 mg/mL concentrations (p???0.01). In the case of antifungal effects of CoNPs, they inhibited the growth of all fungi at 1-4 mg/mL concentrations and destroyed them at 2-16 mg/mL concentrations (p???0.01). The synthesized CoNPs had great cell viability dose-dependently and indicated this method was nontoxic. DPPH free radical scavenging test was done to assess the antioxidant potentials, which revealed similar antioxidant potentials for CoNPs and butylated hydroxytoluene. In vivo experiment, after creating the cutaneous wound, the rats were randomly divided into six groups: untreated control, treatment with Eucerin basal ointment, treatment with 3% tetracycline ointment, treatment with 0.2% Co(NO3)2 ointment, treatment with 0.2% Z. clinopodioides ointment, and treatment with 0.2% CoNPs ointment. These groups were treated for 10 days. For histopathological and biochemical analysis of the healing trend, a 3?×?3 cm section was prepared from all dermal thicknesses at day 10. Use of CoNPs ointment in the treatment groups substantially raised (p???0.01) the wound contracture, hydroxyl proline, hexosamine, hexuronic acid, fibrocyte, and fibrocytes/fibroblast rate and remarkably decreased (p???0.01) the wound area, total cells, neutrophil, and lymphocyte compared to other groups. In conclusion, CoNPs can be used as a medical supplement owing to their non-cytotoxic, antioxidant, antibacterial, antifungal, and cutaneous wound healing effects. Additionally, the novel nanoparticles (Co(NO3)2 and CoNPs) were good inhibitors of the ?-glycosidase, and cholinesterase enzymes.

Dataset Information

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

Background

Methods

Results

Conclusions

Publications

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

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