Microwave assisted the short time clean synthesis of 1,3-diketones as building blocks in heterocyclic synthesis: a facile synthesis and antimicrobial evaluation of new dihydropyridine, 4H-pyrane, dihydropyridazine, pyrimidine and pyrazole derivatives

• Published in: Molecular diversity 2022-04, Vol.26 (2), p.741-755
• Main Authors: Abdel Reheim, Mohamed Ahmed Mahmoud, Abdel Hafiz, Ibrahim Saad, Abdel Rady, Hend Saad Eldin
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Infective Agents - chemistry; Antifungal Agents; Antimicrobial agents; Azoles; Biochemistry; Biomedical and Life Sciences; Candida albicans; Dihydropyridines; Escherichia coli; Fungi; Gram-positive bacteria; Life Sciences; Microbial Sensitivity Tests; Microwaves; Organic Chemistry; Original; Original Article; Pharmacy; Polymer Sciences; Pyrazoles - chemistry; Pyrimidines
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-020-10152-9

The compounds bearing naphthalene moiety can be used as medical preparations because of their wide spectrum of biological activity and low toxicity. In this study, a new series of azoles or azines were synthesized from the reaction of the key intermediate 1-(1-hydroxynaphthalen-2-yl)-3-phenylpropane-1,3-dione 3 with a variety of electrophilic and nucleophilic reagents under a variety of mild conditions. The chemical structures of these compounds were confirmed by various spectroscopic methods such as (IR, 1 H-NMR, 13 C-NMR, mass spectra and elemental analyses). The prepared compounds were screened in vitro for their anti-microbial activity against some species of Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria ( Escherichia coli and Pseudomonas aeuroginosa ). Anti-fungal activities of the compounds were tested against yeast and mycelial fungi, Candida albicans and Aspergillus flavus . The antimicrobial activity of this series was showed either weak or moderate activities. Graphic abstract