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

Rangappa Santosh, Priyodip Paul, Mukunthan KS, Chenthattil Raril, Panchangam M. Krishna, Jamballi G. Manjunatha, Gundibasappa K. Nagaraja

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Dihydropyrimidinones (DHPMs), 4 a-f and 6 a-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), 4 c, 6 d, 6 e, and 6 f showed redox behavior.

Original languageEnglish
Pages (from-to)990-996
Number of pages7
JournalChemistrySelect
Volume4
Issue number3
DOIs
Publication statusPublished - 23-01-2019

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Antioxidants
Derivatives
DNA
Salmonella
Bacilli
Nuclear magnetic resonance
Scavenging
pyrimidine

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Santosh, Rangappa ; Paul, Priyodip ; KS, Mukunthan ; Raril, Chenthattil ; Krishna, Panchangam M. ; Manjunatha, Jamballi G. ; Nagaraja, Gundibasappa K. / One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics. In: ChemistrySelect. 2019 ; Vol. 4, No. 3. pp. 990-996.
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title = "One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics",
abstract = "Dihydropyrimidinones (DHPMs), 4 a-f and 6 a-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), 4 c, 6 d, 6 e, and 6 f showed redox behavior.",
author = "Rangappa Santosh and Priyodip Paul and Mukunthan KS and Chenthattil Raril and Krishna, {Panchangam M.} and Manjunatha, {Jamballi G.} and Nagaraja, {Gundibasappa K.}",
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doi = "10.1002/slct.201803416",
language = "English",
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pages = "990--996",
journal = "ChemistrySelect",
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One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics. / Santosh, Rangappa; Paul, Priyodip; KS, Mukunthan ; Raril, Chenthattil; Krishna, Panchangam M.; Manjunatha, Jamballi G.; Nagaraja, Gundibasappa K.

In: ChemistrySelect, Vol. 4, No. 3, 23.01.2019, p. 990-996.

Research output: Contribution to journalArticle

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T1 - One-Pot Synthesis of Pyrimido[4,5-d]pyrimidine Derivatives and Investigation of Their Antibacterial, Antioxidant, DNA-Binding and Voltammetric Characteristics

AU - Santosh, Rangappa

AU - Paul, Priyodip

AU - KS, Mukunthan

AU - Raril, Chenthattil

AU - Krishna, Panchangam M.

AU - Manjunatha, Jamballi G.

AU - Nagaraja, Gundibasappa K.

PY - 2019/1/23

Y1 - 2019/1/23

N2 - Dihydropyrimidinones (DHPMs), 4 a-f and 6 a-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), 4 c, 6 d, 6 e, and 6 f showed redox behavior.

AB - Dihydropyrimidinones (DHPMs), 4 a-f and 6 a-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), 4 c, 6 d, 6 e, and 6 f showed redox behavior.

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