Antimicrobial activity of n-heterocyclic compounds containing coumarin moiety
Coumarin derivatives with different heterocyclic systems in the position 3 exhibit antibacterial activity. The aim of the work was the synthesis of new coumarin containing heterocyclic ensembles , the study of physical and chemical properties and biological activity of these compounds. As the starting reagent 3-(4-acetylphenyl)-2H-2-chromenone (I) was used. This compound by the reaction of coumarin with 4-acetyl benzenediazonium chloride was synthesized. By bromination of compound (I) 3-[4-(2-bromoacetyl)phenyl]-2H-2-chromenone (II) was obtained. By the reactions of compound (II) with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline and triphenylphosphine a quaternary salts was prepared. Compound (II) reacts with binucleophilic reagents to form thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[2,1-i]purine derivatives. On the base of experimental microbiological studies we have established that compound (II), 3-(4-imidazo[1,2-a]pyrimidin-2-ylphenyl)-2H-2-chromenone (XIII) and 3-[4-(1H-imidazo[2,1-i]purin-8-yl)phenyl]-2H-2-chromenone (XIV) exhibit antimicrobial activity against strain S. aureus ATCC 25923 at low concentrations. Compounds (II, XIV) and 4-(2-oxo-2-[4-(2-oxo-2H-3-chromenyl)phenyl]ethyl)benzo[f]quinolinium bromide (VI) exhibit antimicrobial activity against strain B. subtilis ATCC 6633.
2. Yagodoznets P.I., Skrypskaya O.V., Chernyuk I.N., et al. Synthesis and antimicrobial activity of coumarin-containing imidazoles // Khim.-farm. journ - 1996. - Vol. 30, No. 5. - P. 50-51.
3. Yagodnets P.I., Skrypskaya O.V., Blinder O.V. Synthesis and biological activity of coumarin-containing imidazoles // Pharmac. journ - 2004. - No. 5. - P. 65-67.
4. Yagodnets P. I., Skrypskaya O. V., Blinder O. V. Synthesis and biological activity of onion derivatives of indole and coumarin // Ibid. - 2004. - No. 6. - P. 75-78.
5. Mladenović M., Vuković N., Sukdolak S. et al. Design of Novel 4-Hydroxy-chromene-2-one Derivatives as Antimicrobial Agents // Molecules. - 2010. - V. 15. - pp. 4294-4308.
6. Parameshwar R., Ranganath Y. S., Babu V. H. et al. Synthesis and Antifungal Screening of Some Novel Coumarin Linked Imidazole Derivatives // Res. J. Pharmac. Biologist Chem Sci - 2011. - V. 2, N 3. - P. 514-520.
7. Porwal B., Jayashree B. S., Attimarad M. Synthesis of Some New 3-Coumarinoyl Pyridinium and Quinolinium Bromides for their Antimicrobial Activity // J. Basic and Clinical Pharmacy. - 2010. - V. 1, N 1. - P. 29-32.
8. Vuković N., Sukdolak S., Solujić S. et al. Synthesis and Antimicrobial Evaluation of Some Novel 2-Aminothiazole Derivatives of 4-Hydroxy-chromene-2-one // Arch. Pharm Chem Life Sci. - 2008. - P. 341, N 8. - P. 491-496.
9. Prey V., Kerr B., Berbalk H. Zur Kenntnis der Thiolactone // Monatsh. Chem - 1960. - B. 91, N 5.- S. 774-793.
10. Kaminski J. J., Puchalski C., Solomon D. M. et al. Antiulcer Agents. 4. Conformational Considerations and the Antiulcer Activity of Substituted Imidazo [1,2-a] Pyridines and Related Analogues // J. Med. Chem - 1989. - V. 32, N 8. - R. 1686-1700.
11. Orlenko IV, Kovalenko SN, Zhuravel IA, etc. Ensembles of cycles with coumarin link 4. Synthesis of 3- (imidazo [1,2-a] -pyridinyl-2) -, 3- (imidazo [1,2-a] -pyrimidyl-2) - and 3- (pyrrolo [1,2-a] -pyridinyl-2) coumarins // Physiologically active substances. - 2001. - No. 2. - P. 25-28.
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