One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics

摘要

Dihydropyrimidinones (DHPMs), 4a-f and 6a-f is reported and were characterized by 1 H-NMR, 13 C-NMR, FT-IR and LC-MS. The synthesized compounds were evaluated for their antibacterial activity against Staphylococcus aureus (S.aureus), Bacillus subtilis (B. subtilis), Salmonella typhi (S. typhi) and Pseudomonas aeruginosa (P. aeruginosa). Among the test samples com- pounds, 5-(4-hydroxy-3-methoxyphenyl)-7-imino-1,3,5,6,8-pen- tahydropyrimido[4,5-d]pyrimidine-2,4-dione (6c) and 5-(4- hydroxy-3,5-dimethoxyphenyl)-1,3-N,N-dimethyl-7-thioxo-5,6,8- trihydropyrimido[4,5-d]pyrimidine-2,4-dione (4d) were more potent against S. aureus and B. subtilis. Whereas 5-(4-hydroxy-3- methoxyphenyl)-1,3-N,N-dimethyl-5,6,8-trihydropyrimido[4,5-d] pyrimidine-2,4,7-trione (6e) and 5-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3-N,N-dimethyl-5,6,8-trihydropyrimido[4,5-d]pyrimi- dine-2,4,7-trione (4e) showed good inhibition against S. typhi and P. aeruginosa which were well supported by computational interaction and DNA binding studies. Compound 5-(4-hydroxy- 3,5-dimethoxyphenyl)-7-imino-1,3,5,6,8-pentahydropyrimido [4,5-d]pyrimidine-2,4,7-trione (4c) exhibited potent scavenging activity with IC50 of 8.30 mg/ml. Furthermore, Cyclic Voltam- metric analysis disclosed that 5-(4-hydroxy-3,5-dimethoxyphen- yl)-7-thioxo-1,3,5,6,8-pentahydropyrimido[4,5-d]pyrimidine-2,4- dione (4a), 5-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,5,6,8-penta- hydropyrimido[4,5-d]pyrimidine-2,4,7-trione (4b), 4c, 6d, 6e, and 6f showed redox behavior.