Synthesis and antimicrobial activity of new crown ethers of Schiff base type

Abstract

New crown ether ligands of the Schiff base type (4a–d) were synthesized by the reaction of 2-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde and 2-hydroxy-1-naphthaldehyde with 6,7-dihydro-13H-dibenzo [e,h] [1,4]dioxonin-2,11-diamine (3). The structures of ligands were investigated by elemental analysis as well as IR, UV–visible, 1H-NMR, 13C-NMR and MS spectroscopic data. The antimicrobial and anti-yeast activities of the ligands were screened in vitro against the organisms Escherichia coli ATCC 11230, Staphylococcus aureus ATCC 6538, Klebsiella pneumoniae UC57, Micrococcus luteus La 2971, Proteus vulgaris ATCC 8427, Pseudomonas aeruginosa ATCC 27853, Mycobacterium smegmatis CCM 2067, Bacillus cereus ATCC 7064, Listeria monocytogenes ATCC 15313, Candida albicans ATCC 10231, Kluyveromyces fragilis NRRL 2415, Rhodotorula rubra DSM 70403, Debaryomyces hansenii DSM 70238 and Hanseniaspora guilliermondii DSM 3432.

Keywords

• crown ether
• Schiff base
• antimicrobial activity
• spectroscopy