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

Autor: Jamballi G. Manjunatha, Priyodip Paul, Mukunthan K. Selvam, Panchangam Murali Krishna, Gundibasappa Karikannar Nagaraja, Rangappa Santosh, Chenthattil Raril
Rok vydání: 2019
Předmět:
Zdroj: ChemistrySelect. 4:990-996
ISSN: 2365-6549
DOI: 10.1002/slct.201803416
Popis: Dihydropyrimidinones (DHPMs), 4a-f and 6a-f is reported and were characterized by 1H-NMR, 13C-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 compounds, 5-(4-hydroxy-3-methoxyphenyl)-7-imino-1,3,5,6,8-pentahydropyrimido[ 4,5-d]pyrimidine-2,4-dione (6 c) 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 (4 d) 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 (6 e) and 5-(4-hydroxy-3,5-dimethoxyphenyl)- 1,3-N,N-dimethyl-5,6,8-trihydropyrimido[4,5-d]pyrimidine- 2,4,7-trione (4 e) 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 (4 c) exhibited potent scavenging activity with IC50 of 8.30 mg/ml. Furthermore, Cyclic Voltammetric analysis disclosed that 5-(4-hydroxy-3,5-dimethoxyphenyl)- 7-thioxo-1,3,5,6,8-pentahydropyrimido[4,5-d]pyrimidine-2,4- dione (4 a), 5-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,5,6,8-pentahydropyrimido[ 4,5-d]pyrimidine-2,4,7-trione (4 b), 4c, 6d, 6e, and 6f showed redox behavior
Databáze: OpenAIRE