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Efficient one-pot protocol for diverse pyrazolylphosphonates by multi-component reactions: their antioxidant and antibacterial activities

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Abstract

Efficient one-pot three-component reactions of pyrazolones with arylaldehydes and triethyl phosphite were carried out in the presence of ethylenediammonium diacetate as catalyst to synthesize biologically interesting pyrazolylphosphonate derivatives. This methodology offers several significant advantages such as environmentally benign character, the use of a mild catalyst, high yields, and ease of handling. The synthesized compounds were screened for their antioxidant and antibacterial activities. The result showed that compound 4d \((\hbox {IC}_{50 }= 3.40\,\upmu \hbox {M})\) exhibited a strong free radical scavenger toward DPPH free radicals compared with standard BHT \((\hbox {IC}_{50 } = 29.23\,\upmu \hbox {M})\). In addition, compounds 4e and 4p showed potent antibacterial activities against Gram-negative bacteria of E. coli and compound 4o exhibited a potent activity against Gram-positive bacteria of S. aureus compared with standard Ampicillin.

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Acknowledgments

This work was supported by Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2014R1A6A1031189).

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  1. School of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea

    So Rang Kang & Yong Rok Lee

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  1. So Rang Kang
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Correspondence to Yong Rok Lee.

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Kang, S.R., Lee, Y.R. Efficient one-pot protocol for diverse pyrazolylphosphonates by multi-component reactions: their antioxidant and antibacterial activities. Mol Divers 19, 293–304 (2015). https://doi.org/10.1007/s11030-015-9568-4

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  • DOI: https://doi.org/10.1007/s11030-015-9568-4

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