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SYNTHESIS OF SOME PYRIDINE, PYRIMIDINE AND CYCLOHEXENONE DERIVATIVES AS ANTIBACTERIAL AGENTS

Nehad A. Abdel Latif , Manal M. Saeed , Nesreen S. Ahmed Rasha Z. Batran and Nadia R. A. El-Mouhty

The present research work describes the synthesis of new heterocyclic compounds using khellinone methyl ether (1) as a starting material. Compound (1) allowed to react with different aldehydes namely, benzaldehyde, p-methoxy benzaldehyde and p-nitro benzaldehyde to give the corresponding chalcones (2a-c). The latter compounds reacted with malononitrile, guanidine, ethylcyanoacetate and ethylacetoacetate to yield cyanopyridine, aminopyrimidine, cyanopyridone and cyclohexenone derivatives (3a-c), (4a-c), (5a-c) and (6a-c) respectively. When (2a-c) allowed to react with urea and thiourea, they gave oxopyrimidine and thioxopyrimidine derivatives (7a-c) and (8a-c). On the other hand compound (8a-c) condensed with 3-bromopropionic acid or chloroacetic acid to yield thiazinopyrimidine (9a-c) and 3- thiazolo-pyrimidine (10a-c) respectively. Compounds (8a-c) were condensed with chloroacetic acid and aromatic aldehyde to yield the aryl methylene derivatives (11a-c) which could be prepared directly by condensation of compound (10a-c) with aromatic aldehyde. The characterization of the resulting products were confirmed by FTIR, 1HNMR, MS and elemental analyses. The newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Pseudomonas aurignosa, Salmonella typhimurium, Bacillus subtilis and Staphylococcus aureus using the disc diffusion method.