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Synthesis, structure and antibacterial activity of 3-substituted derivatives of 4-hydroxycoumarin

DAVORKA ZAVRŠNIK ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Čekaluša 90, 71000 Sarajevo, Bosnia and Herzegovina
SELMA ŠPIRTOVIĆ-HALILOVIĆ ; 1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Čekaluša 90, 71000 Sarajevo, Bosnia and Herzegovina
DŽENITA SOFTIĆ ; 2Agency for Medicinal Products and Medical Devices of Bosnia and Herzegovina, The Control Laboratory of the Agency, Titova 9, Sarajevo, Bosnia and Herzegovina

Sažetak

Background and purpose: Having in mind the results of our previous
work, which suggested antimicrobial activity of some 3-cynnamoyl-4-hydroxycoumarins, we carried out the synthesis of several new derivatives of this group. The microbiological activity of compounds was tested by the diffusion and dilution methods on various species of bacteria. The aim of the study was to evaluate the influence of the substituents on antimicrobial activity.

Material and methods: A series of new 3-cynnamoyl-4-hydroxycoumarins was prepared by the reaction of nucleophylic addition from 3--acetyl-4-hydroxycoumarin acting on appropriate aromatic aldehydes. The microbiological activity of compounds was tested by the diffusion and dilution methods on species of bacteria Pseudomonas aeruginosa, Echerichia coli, Salmonella typhimurium, Bordatella bronchiseptica, Bacillus subtilis, and Staphyloccocus aureus.

Results: The synthesis of new 3-cynnamoyl-4-hydroxycoumarins was
carried out. The elementary content of the synthesized compounds was confirmed by elementary analysis, and structures were confirmed with IR--spectrophotometry and 1H-NMR spectrophotometry. The compounds that have halogens showed the best microbiological activity. Compounds 5, and 6 were the most effective against Bacillus subtilis (MBC=0.0039 mg/mL, andMIC=of 0.0010 mg/mL. Compound 6 was the most effective against Staphylococcus aureus (MBC=0.0156 mg/mL,
and MIC = of 0.0019 mg/mL).

Conclusion: All synthesized compounds have larger or smaller growth
inhibition zones when it comes to Gram-positive aerobe bacteria Bacillus subtilis and Staphyloccocus aureus. The tested compounds showed resistance to Gram-negative types of bacteria. The compounds that have halogens, as substituents (compound 5 and 6) showed the best microbiological activity.

Ključne riječi

Hrčak ID:

67271

URI

https://hrcak.srce.hr/67271

Datum izdavanja:

31.3.2011.

Posjeta: 3.839 *