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Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents

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Abstract

New phenolic derivatives bearing hydrazine and 1,3,4-oxadiazole moieties were synthesized and evaluated for their in vitro antimicrobial and antioxidant activities. Most of the compounds revealed pronounced activity against Pseudomonas aeruginosa as well as promising antioxidant activities. N 1-(2,5-Dihydroxybenzoyl)-N 2-(4-methylphenylsulfonyl)hydrazine displayed promising activity against Escherichia coli and P. aeruginosa. N 1-(2,5-Dihydroxybenzoyl)-N 2-(2-naphthalenylmethylene)hydrazine was almost equipotent to the standard antioxidant vitamin C having scavenging activities of 84 and 93%, respectively. In vitro cytotoxicity study revealed that N 1-(2,5-dihydroxybenzoyl)-N 2-(2,3,4-trimethoxyphenylmethylene)hydrazine, N 1-(2,5-dihydroxybenzoyl)-N 2-(3,4,5-trimethoxyphenylmethylene)hydrazine, and N 1-(2,5-dihydroxybenzoyl)-N 2-(4-methylphenylsulfonyl)hydrazine are more safe than reference 5-fluorouracil. In silico drug relevant properties proposed that all compounds have high to moderate drug-likeness scores. Accordingly, these derivatives can be potential leads for development of potent antimicrobial and antioxidant agents.

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Acknowledgements

Authors thank the University of Helsinki, Finland for doing part of the chemistry work, NMR and IR spectra.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, 21521, Egypt

    Ibrahim Chaaban, El Sayeda M. El Khawass, Heba A. Abd El Razik & Nehad S. El Salamouni

  2. Department of Biochemistry, Faculty of Science, Alexandria University, Alexandria, Egypt

    Doaa A. Ghareeb

  3. Medical Biotechnology Department, Genetic Engineering and Biotechnology Research Institute (GEBRI), City for Scientific Research and Technology Application, Borg El-Arab, Alexandria, Egypt

    Abeer E. Abdel Wahab

Authors
  1. Ibrahim Chaaban
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  2. El Sayeda M. El Khawass
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  3. Heba A. Abd El Razik
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  4. Nehad S. El Salamouni
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  5. Doaa A. Ghareeb
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  6. Abeer E. Abdel Wahab
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Correspondence to Nehad S. El Salamouni.

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Chaaban, I., El Khawass, E.S.M., Abd El Razik, H.A. et al. Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents. Monatsh Chem 149, 127–139 (2018). https://doi.org/10.1007/s00706-017-1983-z

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  • DOI: https://doi.org/10.1007/s00706-017-1983-z

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