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Design and synthesis of novel quinazolinyl-bisspirooxindoles as potent anti-tubercular agents: an ultrasound-promoted methodology

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Abstract

The essential need for the potent anti-tubercular (anti-TB) agents with high selectivity and safety profile prompted us to synthesize a new series of quinazolinyl-bisspirooxindoles. The title compounds were synthesized by one-pot multicomponent [3 + 2] cycloaddition reaction under ultrasonication. Further, in vitro anti-TB activity was evaluated against Mycobacterium tuberculosis H37Rv. Among the screened compounds, two compounds (4q and 4x) showed potent activity with MIC value 1.56 µg/mL and four compounds exhibited significant activity (MIC = 3.125 µg/mL), and also cytotoxicity studies against RAW 264.7 cell lines reveal that most active compounds were less toxic to humans. In addition, in order to demonstrate the inhibitory properties, molecular docking studies were carried out and the results showed that the target compounds have good binding energy and better binding affinity within the active pocket, thus these compounds may consider to be as potent inhibitors toward selective targets.

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Acknowledgements

The authors B. S. A. and S. B. thank the Director, NIT Warangal for providing the facilities. B. S. A. thanks the UGC New Delhi, India for providing Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology Warangal, Hanamkonda, Telangana, 506 004, India

    Bhargava Sai Allaka & Srinivas Basavoju

  2. Department of Pharmacy, Birla Institute of Technology and Science-Pilani, Hyderabad, Telangana, 500 078, India

    Estharla Madhu Rekha & Dharmarajan Sriram

  3. Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, Maharashtra, 411 008, India

    Gamidi Rama Krishna

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  1. Bhargava Sai Allaka
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Correspondence to Srinivas Basavoju.

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Allaka, B.S., Basavoju, S., Madhu Rekha, E. et al. Design and synthesis of novel quinazolinyl-bisspirooxindoles as potent anti-tubercular agents: an ultrasound-promoted methodology. Mol Divers 27, 1427–1436 (2023). https://doi.org/10.1007/s11030-022-10500-x

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