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Synthesis, characterization, antioxidant, and antibacterial activities of new 2,3-dimethoxy and 3-acetoxy-2-methyl benzamides

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Abstract

We performed a series of novel benzamide compounds which were synthesized starting from 2,3-dimethoxybenzoic acid or 3-acetoxy-2-methylbenzoic acid and amine derivatives. All the obtained products were purified, and the analysis of these products was determined with IR, 1H NMR, 13C NMR spectroscopic, and elemental methods. The in vitro antioxidant activity of all the compounds was determined by total antioxidant, free radical scavenging, and metal chelating activity. Some of synthesized compounds showed more effective total antioxidant, free radical scavenging, and metal chelating activity compared with standards. One of the benzamide compounds has been shown to exhibit effective metal chelate activity. The new compounds were determined in vitro antibacterial activity against three gram-positive bacteria and three gram-negative bacteria and compared with two control drugs. Thus, by conducting in vivo biochemical tests of effective amides, researches can be carried out in different fields of application.

Graphic abstract

We performed a series of novel benzamide compounds which were synthesized, and the analysis of these products was determined with IR, 1H NMR, 13C NMR spectroscopic, and elemental methods. The in vitro antioxidant activity of all the compounds was determined by total antioxidant, free radical scavenging, and metal chelating activity. All the compounds were tested for their in vitro growth inhibitory activity against different bacteria.

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Acknowledgements

This study was supported by Ondokuz Mayıs University as a Scientific Research Project (PYO.FEN.1904.18.018). We would like to thank Dr. Mohammad Maher Jesry for checking and proofreading the article. Moreover, we would like to thank research assistant Yavuz Derin for taking the NMR spectra.

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Authors and Affiliations

  1. Department of Chemistry Education, Faculty of Education, Ondokuz Mayis University, 55139, Atakum, Samsun, Turkey

    Hasan Yakan

  2. Environmental Health Programme, Vocational School, Sinop University, 5700, Sinop, Turkey

    Sukriye Cakmak

  3. Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139, Atakum, Samsun, Turkey

    Halil Kutuk, Semiha Yenigun & Tevfik Ozen

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  1. Hasan Yakan
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  2. Sukriye Cakmak
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  3. Halil Kutuk
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  4. Semiha Yenigun
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  5. Tevfik Ozen
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Correspondence to Hasan Yakan or Tevfik Ozen.

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Yakan, H., Cakmak, S., Kutuk, H. et al. Synthesis, characterization, antioxidant, and antibacterial activities of new 2,3-dimethoxy and 3-acetoxy-2-methyl benzamides. Res Chem Intermed 46, 2767–2787 (2020). https://doi.org/10.1007/s11164-020-04118-7

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