Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7-hydroxycoumarinyl moieties

Autor: Alicja Sztokfisz-Ignasiak, Magdalena Tomczyk, Elżbieta Hejchman, Izabela Mlynarczuk-Bialy, Barbara Sowirka-Taciak, Jan Jankowski, Dorota Maciejewska, Hanna Kruszewska
Rok vydání: 2019
Předmět:
Zdroj: Monatshefte für Chemie - Chemical Monthly. 150:255-266
ISSN: 1434-4475
0026-9247
DOI: 10.1007/s00706-018-2325-5
Popis: 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.
Databáze: OpenAIRE
Externí odkaz: