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Design, synthesis, biological evaluation and in silico molecular docking studies of novel benzochromeno[2,3-d]thiazolopyrimidine derivatives

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Abstract

A new series of benzochromeno[2,3-d]thiazolopyrimidine derivatives were synthesized by involving 7-phenyl-10-thioxo-7,9,10,11-tetrahydro-8H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-ones with phenacyl bromide in the presence of p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions which furnished good yields. All these synthesized compounds (7a–k) were screened for their in vitro antibacterial activity against two gram positive bacteria such as (Staphylococcus aureus, Staphylococcus pyogenes) and two gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and also evaluated for their antifungal activity against four pathogenic fungal strains. All these compounds displayed good antibacterial and antifungal activity compared to reference drugs such as ciprofloxacin and mycostatin. Predominantly 7f, 7e and 7b compounds showed the highest antibacterial and antifungal activities. Moreover, all the synthesized compounds were docked against topoisomerase II DNA gyrase enzyme, which is a crucial drug target in bacteria. Docking results showed that π–π stacking and π-cationic interactions were responsible for binding interactions with the target protein.

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Acknowledgements

We gratefully acknowledge the head of the Department of Chemistry, Osmania University, for providing research facilities. One of the authors (B. Sonyanaik) thanks the University Grant Commission (UGC) New Delhi, India, for providing senior research fellowship.

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Authors and Affiliations

  1. Medicinal Chemistry Laboratory, Department of Chemistry, Osmania University, Tarnaka, Telangana State, 500007, India

    Sonyanaik Banoth & Sakram Boda

  2. National Institute of Nutrition, Tarnaka, Telangana State, 500007, India

    Shyam Perugu

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

    Saikrishna Balabadra & Vijjulatha Manga

Authors
  1. Sonyanaik Banoth
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  2. Sakram Boda
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  3. Shyam Perugu
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  4. Saikrishna Balabadra
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  5. Vijjulatha Manga
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Corresponding author

Correspondence to Sakram Boda.

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Banoth, S., Boda, S., Perugu, S. et al. Design, synthesis, biological evaluation and in silico molecular docking studies of novel benzochromeno[2,3-d]thiazolopyrimidine derivatives. Res Chem Intermed 44, 1833–1846 (2018). https://doi.org/10.1007/s11164-017-3201-3

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