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Synthesis of azo dyes possessing N-heterocycles and evaluation of their anticancer and antibacterial properties

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Abstract

A series of 4-(1-azolyl)aniline derivatives (azole = imidazole, benzimidazole, pyrazole, 3-methylpyrazole, and 4-methylpyrazole) underwent diazotization reaction by NaNO2/HCl. The diazonium salts were consequently treated with aromatics such as phenol, N,N-dimethylaniline, 2-naphthol, and 8-hydroxyquinoline to give the coupled azo compounds. The antibacterial activities of some of the products were evaluated against Gram-negative [Escherichia coli (ATCC 25922)] and Gram-positive [Staphylococcus aureus (ATCC 25923)] bacteria. Moreover, in vitro examinations for a series of the products corroborated anticancer activities against MCF7 breast cancer cells.

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Acknowledgements

The authors thank Research Affairs of University of Tabriz, Iran, and also Tabriz University of Medical Sciences, Iran, for financial supports.

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Authors and Affiliations

  1. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, 5166614766, Iran

    Zarrin Ghasemi & Sajjad Azizi

  2. Research Center for Pharmaceutical Nanotechnology and School of Advanced Medical Science, Tabriz University of Medical Sciences, Tabriz, Iran

    Roya Salehi

  3. Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran

    Hossein Samadi Kafil

Authors
  1. Zarrin Ghasemi
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  2. Sajjad Azizi
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  3. Roya Salehi
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  4. Hossein Samadi Kafil
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Correspondence to Zarrin Ghasemi.

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Ghasemi, Z., Azizi, S., Salehi, R. et al. Synthesis of azo dyes possessing N-heterocycles and evaluation of their anticancer and antibacterial properties. Monatsh Chem 149, 149–157 (2018). https://doi.org/10.1007/s00706-017-2073-y

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  • DOI: https://doi.org/10.1007/s00706-017-2073-y

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