Abstract
18 (11 novel) Schiff bases, derivatives of salicylaldehyde, 2-hydroxyacetophenone, and 6-acetyl-, 8-acetyl-, and 8-formyl-7-hydroxy-4-methylcoumarin were synthesized and characterized by their spectral studies. 6-Acetyl-7-hydroxy-4-methylcoumarin was prepared by novel method under microwave assistance. These Schiff bases were evaluated for antibacterial activities against 12 bacterial and six fungi strains in vitro. N-(3,5-Dichloro-2-hydroxybenzylidene)-4-aminobenzenesulfonic acid sodium salt proved to be the most active against Staphylococcus aureus and MRSA strains (MIC 0.0194 µmol/cm3). The substitution pattern, two chlorine atoms in the salicylidene ring and the SO3Na group, is probably the most beneficial for the activity against Gram-(+) bacteria strains. All Schiff bases were evaluated for cancer efficacy against CFPAC-1 and HeLa cell cultures originating from human pancreas cancer or human cervical cancer. Schiff bases derived from salicylaldehyde are highly effective in pancreas and cervical cancer cells; however, they demonstrate also substantial toxicity towards NIH3T3 cells. Derivatives of coumarin contain three highly selective compounds: 7-hydroxy-8-[(4-methoxyphenylimino)methyl]-4-methyl-2H-chromen-2-one, N-[(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene]-4-aminobenzenesulfonic acid sodium salt, and 7-hydroxy-8-[1-(4-hydroxyphenylimino)ethyl]-4-methyl-2H-chromen-2-one suggesting more promising potential of the second group of substances.Graphical abstract
Highlights
Schiff bases, formed in the reaction of aromatic or heteroaromatic substances’ primary amine with aldehyde or ketone, are classified as imines or azomethines
To the best of our knowledge, there are no data concerning the biological activity of Schiff bases having benzenesulfonic acid salt moiety combined with halogenated salicylidene or 7-hydroxycoumarin scaffolds
In the present study, we report the synthesis, characterization, and in vitro cytotoxic and antimicrobial evaluation of a series of hybrid Schiff bases, derived from salicylaldehyde or 7-hydroxycoumarin scaffold and para-substituted aniline, with a view to explore their potency as better chemotherapeutic agents (Fig. 4)
Summary
Schiff bases, formed in the reaction of aromatic or heteroaromatic substances’ primary amine with aldehyde or ketone, are classified as imines or azomethines. They are a significant class of compounds in medicinal and pharmaceutical chemistry having a variety of biological applications that include antibacterial, antifungal, and antitumor activities. The increase in the mortality rate associated with infectious diseases is directly related to antimicrobial resistance to antibiotics [5]. Schiff bases have been shown to be interesting moieties for the design of antimicrobial agents [1–4]. Several Schiff bases having dichloro or bromophenyl moieties have been proved to be biologically important [4]. Salicylidene (2-hydroxybenzaldehyde-derived) Schiff bases (Fig. 1) are reported as promising antimicrobial drugs [4, 8, 9]
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