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Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents

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Abstract

A series of new flavone/isoxazole fused heterocycles 5a–f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a–t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial activity using turbidometric assay. The majority of the tested compounds exhibited antiproliferative activity and antimycobacterial activity. Compounds 7l, 7q and 7r showed moderate antiproliferative activity with IC50 values 17.9, 14.2, 19.1 \(\upmu \hbox {M}\), respectively, and compound 5a showed moderate antimycobacterial activity with 41.7% of inhibition at 30 \(\upmu \hbox {M}\) concentration.

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Acknowledgements

The authors are thankful to Vetindia pharmaceuticals Ltd, Leavo chem. Laboratories for providing laboratory facilities to carry out this work.

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Authors and Affiliations

  1. Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, India

    Yerrabelly Jayaprakash Rao & Gogula Thirupathi

  2. Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, India

    Thummala Sowjanya

  3. Department of Chemistry, Palamuru University, Mahabubnagar, India

    Nandula Yadagiri Sreenivasa Murthy

  4. Centre for Chemical Biology, Indian Institute of Chemical Technology, Hyderabad, India

    Sudha Sravanti Kotapalli

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  1. Yerrabelly Jayaprakash Rao
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  2. Thummala Sowjanya
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  5. Sudha Sravanti Kotapalli
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Correspondence to Yerrabelly Jayaprakash Rao.

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Rao, Y.J., Sowjanya, T., Thirupathi, G. et al. Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents. Mol Divers 22, 803–814 (2018). https://doi.org/10.1007/s11030-018-9833-4

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  • DOI: https://doi.org/10.1007/s11030-018-9833-4

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