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Novel 1,3-Indenedione-Based Azo Dyes: Synthesis, Characterization, Solvatochromic UV-Vis Absorption Study, and Biological Activity

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Abstract

In this work, we reported the synthesis of novel indanedione-based azo dyes by a conventional diazo coupling reaction at 0–5°C. The synthesized dyes were characterized by using different spectroscopic techniques like FT-IR, 1H NMR and HRMS. The indanedione-based azo dyes were examined for cytotoxic activity against MIAPaCa-2 pancreatic cancer cell lines. 2-[(E)-1,3-Benzothiazol-2-yldiazenyl]-1H-indene-1,3(2H)-dione showed a good reduction in cell viability against MIAPaCa-2 cell line in a concentration dependent manner compared to other compounds. Further, the synthesized azo dyes were screened for DPPH radical scavenging activity in which 2-[(E)-1,3-thiazol-2-yldiazenyl]-1H-indene-1,3(2H)-dione, 2-[(E)-(6-ethoxy-1,3-benzothiazol-2-yl)diazenyl]-1H-indene-1,3(2H)-dione, and 2-[(E)-(4-nitrophenyl)diazenyl]-1H-indene-1,3(2H)-dione showed good scavenging activity with IC50 values of 116.68±1.2, 20.73±7.54 and 129.49±34.25 µg/mL when compared to standard. Furthermore, synthesized indanedione-based azo dyes exhibited appreciable binding affinity with the HIF-1 receptor. Among the synthesized compounds, 2-[(E)-(4-nitrophenyl)diazenyl]-1H-indene-1,3(2H)-dione exhibited a higher binding affinity (–8.9 kcal/mol) by establishing two hydrogen bonds.

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ACKNOWLEDGMENTS

Authors are thankful to the Chairman, Department of Chemistry, Kuvempu University for providing the laboratory facilities and to the University of Mysore for providing spectroscopic study facility.

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Department of P.G. Studies and Research in Chemistry, Jnana Sahyadri, Kuvempu University Shankaraghatta, 577451, Shivamogga, India

    P. V. Navaneethgowda, Y. D. Bodke & B. Manjunatha

  2. Laboratory of Experimental Medicine, Department of Biotechnology, Jnana Sahyadri, Kuvempu University, Shankaraghatta, 577451, Shivamogga, India

    H. M. Kumaraswamy & P. Meghana

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  1. P. V. Navaneethgowda
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  2. Y. D. Bodke
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Navaneethgowda, P.V., Bodke, Y.D., Manjunatha, B. et al. Novel 1,3-Indenedione-Based Azo Dyes: Synthesis, Characterization, Solvatochromic UV-Vis Absorption Study, and Biological Activity. Russ J Gen Chem 93 (Suppl 4), S876–S884 (2023). https://doi.org/10.1134/S1070363223170048

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