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Six-substituted benzothiazole based dispersed azo dyes having antipyrine moiety: synthesis, characterization, DFT, antimicrobial, anticancer and molecular docking studies

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Abstract

A series of benzothiazole based dispersed azo compounds were synthesized by diazotization of benzothiazole derivatives coupling with antipyrine through traditional electrophilic substitution reaction in the temperature range of 0–5 °C. The chemical structure of the prepared molecules (4a–f) was characterized by various analytical and spectroscopic techniques. Further, the theoretical vibrational and structural optimization studies of the molecules 4a–f were investigated by using DFT/B3LYP method. All the synthesized azo dyes were evaluated for their in vitro antimicrobial activities against various bacterial and fungal strains, and the obtained results were exhibited to be potent antimicrobial activities compared with the reference compound. Further, the molecular docking studies have been performed and results showed the possible interaction between the synthesized chemical compound and the receptor. In addition, the in vitro anticancer activity of all the synthesized azo dyes was performed against different human cancer cell lines such as A549, K562 and MDA-MB-231 by using MTT assay.

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Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

Authors are grateful to the department of chemistry, Kuvempu University, for given that the laboratory as well as instrumentation facilities like UV–vis and FTIR. Authors are thankful to SAIF Panjab University and the Department of Physics, M. S. Ramaiah Institute of Technology, Bengaluru for providing the spectral analysis and fluorescence data, respectively. The author Mr. Maliyappa M R is gratefully acknowledged to the University Grant Commission-Basic Science Research (UGC-BSR), New Delhi for providing the financial assistance. The award letter number and date: F. 7-229/ (2009)/dated: 05-11-2015.

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Authors and Affiliations

  1. Department of PG Studies and Research in Chemistry, Kuvempu University, Jnanasahyadri, Shankaragatta, Shivamogga, Karnataka, 577451, India

    M. R. Maliyappa & J. Keshavayya

  2. Frameworks Solids Laboratory, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bengaluru, 560012, India

    Mohammed Azeezulla Nazrulla

  3. Adichunchanagiri Institute for Molecular Medicine, Adichunchanagiri Institute of Medical Sciences, BG Nagara, Mandya, 571448, India

    M. S. Sudhanva & Shobith Rangappa

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  1. M. R. Maliyappa
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  2. J. Keshavayya
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  3. Mohammed Azeezulla Nazrulla
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  4. M. S. Sudhanva
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  5. Shobith Rangappa
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Contributions

Conceptualization was contributed by KJ. Methodology was contributed by MMR. Formal analysis and investigation were contributed by MMR. Writing—original draft preparation, was contributed by MMR. Writing—review and editing, was contributed by MMR, MAN, SMS, SR. Funding acquisition was contributed by MMR. Resources was contributed by MMR. Supervision was contributed by KJ.

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Correspondence to J. Keshavayya.

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Maliyappa, M.R., Keshavayya, J., Nazrulla, M.A. et al. Six-substituted benzothiazole based dispersed azo dyes having antipyrine moiety: synthesis, characterization, DFT, antimicrobial, anticancer and molecular docking studies. J IRAN CHEM SOC 19, 3815–3835 (2022). https://doi.org/10.1007/s13738-022-02569-w

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