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Microwave assisted synthesis, biological evaluation, and molecular docking of novel chroman scaffolds incorporating spirochromanone framework

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Abstract

A series of novel chroman scaffold incorporate spirochromanone derivatives were synthesized from 2-hydroxyacetophenone and cyclic alkanones under microwave irradiation in good yields. Newly synthesized compounds were characterized by analytical and spectral (IR, proton nuclear magnetic resonance, 13C nuclear magnetic resonance, and mass spectrometry) methods. The synthesized compounds were evaluated for their antioxidant and anti-inflammatory activities and were compared with standard drugs. Among all the synthesized compounds 3d (6.09), 3g (5.32), 3h (2.03), 4a (1.17), 4b (0.50), 4c (6.59), 4d (7.86), 4e (6.85), 4f (4.82), and 4g (6.59) were exhibited higher antioxidant activity comparable to that of ascorbic acid (IC50 8.64 µM). The compounds 3a, 3b, 3c, 4c, and 4d were found to have good anti-inflammatory activity. The binding mode of the titled compounds has been proposed based on the molecular docking studies.

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Acknowledgments

The authors are grateful to Department of Chemistry, Osmania University for providing laboratory facilities, and CFRD, OU for providing spectral analysis. One of the authors, Mohan Gandhi Devulapally is thankful to UGC-New Delhi for granting Senior Research Fellowship.

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Authors and Affiliations

  1. Green and Medicinal Chemistry Lab, Department of Chemistry, Osmania University, Hyderabad, Telangana, 50007, India

    Dongamanti Ashok, Devulapally Mohan Gandhi, Aamate Vikas Kumar & Gundu Srinivas

  2. Department of Pharmaceutical Chemistry, Vaageswari College of Pharmacy, Thimmapur, Karimnagar, Telangana, 505481, India

    Malladi Srinivas Reddy

  3. Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, Osmania University, Hyderabad, Telangana, 500007, India

    Sivan Sree Kanth & Manga Vijjulatha

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  1. Dongamanti Ashok
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  2. Devulapally Mohan Gandhi
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  3. Aamate Vikas Kumar
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  4. Gundu Srinivas
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  5. Malladi Srinivas Reddy
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Correspondence to Dongamanti Ashok.

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Ashok, D., Gandhi, D.M., Kumar, A.V. et al. Microwave assisted synthesis, biological evaluation, and molecular docking of novel chroman scaffolds incorporating spirochromanone framework. Med Chem Res 25, 2882–2894 (2016). https://doi.org/10.1007/s00044-016-1699-3

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  • DOI: https://doi.org/10.1007/s00044-016-1699-3

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