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

Chemistry Central Journal

Mahboubeh Kamali Deljoo¹  Reza Aryan¹  Hamid Beyzaei¹  Mohammad Mehdi Zahedi²  Behzad Ghasemi³  Mohammadreza Moghaddam-Manesh⁴ 

[1] Department of Chemistry, Faculty of Science, University of Zabol;Department of Chemistry, University of Saskatchewan;Torbat Jam Faculty of Medical Sciences;Young Researchers and Elite Club, Kerman Branch, Islamic Azad University;

关键词: Antibacterial activity;    Antifungal property;    Antioxidant effect;    Isoxazole;    Multicomponent synthesis;   

DOI  :  10.1186/s13065-018-0488-0

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown