Poly(4-vinylpyridine) Catalyzed Synthesis and Characterization of Pyrano[2,3-d]pyrimidine Derivatives as Potent Antibacterial Agents

Author(s): Tayebeh S. Mokhtari, Mohammad A. Amrollahi*, Enayatollah Sheikhhosseini, Hassan Sheibani, Shahla S. Nezhad.

Journal Name: Current Bioactive Compounds

Volume 14 , Issue 1 , 2018

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Abstract:

Background: A variety of methods have been reported for the synthesis of pyrano[2,3- d]pyrimidines in the literature. Many of these methods are associated with some limitations and generally need expensive or non-available reagents, prolonged reaction times and high temperatures. Thus, the introduction of new methods and /or further work on technical improvements to overcome these limitations is still needed. Pyrano[2,3-d]pyrimidines were prepared by condensation reaction of aldehyde, malononitrile and barbituric acid or 2-thiobarbituric acid by a new efficient procedure and antibacterial activity of selected products was evaluated.

Methods: A mixture of barbituric acid or thiobarbituric acid (2 mmol) aldehyde (2 mmol), and malononitrile (2 mmol)) in the presence of poly (4-vinylpyridine) (0.10 g) was refluxed in H2O:EtOH H2O:EtOH under normal and ultrasonic irradiation conditions for appropriate time. After cooling, the resulting precipitate was filtered, and the crude product was purified by recrystalization from EtOH:H2O to obtain a pure product. Antibacterial activity of products was evaluated using Staphylococcus aureus, Bacillus cereus, Pseudomonasn aeruginosa, and Escherichia coli bacteria strains.

Results: 2,4-Dioxo-1H-pyrano[2,3-d]pyrimidine and 4-oxo-2-thioxo-1H-pyrano[2,3-d]pyrimidine derivatives were synthesized under the optimized conditions. In all cases, the reactions proceeded efficiently at reflux temperature in H2O:EtOH to afford the corresponding products. All the products were characterized by mp. IR, 1H- and 13C-NMR spectra. Antibacterial activity of selected synthesized pyrano[2,3- d]pyrimidines was tested against gram-positive and gram-negative bacteria strains. The verification of antibacterial screening data revealed that the selected compounds have bactericidal properties against Staphylococcus aureus, Bacillus cereus, Pseudomonasn aeruginosa, and Escherichia coli bacteria strains.

Conclusion: We have developed an efficient procedure for the synthesis of pyrano[2,3-d]pyrimidine derivatives via three-component condensation of aromatic aldehydes, malononitrile and barbituric acid or thiobarbituric acid in two different reaction conditions in the presence of catalytic amount of a cheap and readily available catalyst poly (4-vinylpiridine). The bacterial activity study revealed that two compounds showed moderate to good antibacterial activities.

Keywords: Antibacterial active, biologically active, poly(4-vinylpyridine), pyrano[2, 3-d]pyrimidine, three-component reaction, ultrasonic irradiation.

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Article Details

VOLUME: 14
ISSUE: 1
Year: 2018
Page: [54 - 59]
Pages: 6
DOI: 10.2174/1573407213666170104153128

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