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Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents

  • P. Asha Bhanu
  • B. China Raju
  • Y. Jayavardhana Rao
  • G. Narasimha
  • B. Kesava RaoEmail author
Original Research
  • 15 Downloads

Abstract

The present study is aimed to synthesize the novel 7-hydroxyflavanone derived compounds and to assess their biological activity. Two series of compounds such as 2-phenyl-7-((3-phenylisoxazol-5-yl)methoxy)chroman-4-ones (6a–h) and 4-oxo-2-phenylchroman-7-yl acrylates (8a–k) were synthesized from 7-hydroxyflavanone. All the compounds were subjected to anti-microbial activity and molecular docking studies. The results showed that the compounds 6e, 6g–h, 8h–i and 8k were exhibited most potent anti-microbial activity when compared with the standard drugs. Further, the docking studies revealed that the compounds 6a and 8h have the highest binding affinity score of sterol 14-α demethylase and DNA gyrase B respectively. This is the first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity.

Series of 7-hydroxyflavanone based novel isoxazoles 6a–h and acrylates 8a–k were synthesized. Isoxazole compounds 6e, 6g–h and acrylates 8h–i and 8k were identified as most potent anti-microbial agents.

Keyword

7-Hydroxyflavanone Isoxazoles Acrylates Anti-microbial activity DNA gyrase 

Notes

Acknowledgements

PAB thanks Acharya Nagarjuna University and UGC-RGNF (F1-17.1/2016-17/RGNF-2015-17-SC-AND-6403) for providing the facilities and financial support. PAB thank the Director, CSIR-IICT, Hyderabad for providing the laboratory facility to carry out the chemical experiments and analytical support. We also thank Prof. D.V.R. Sai Gopal, Head, Department of Virology, S.V. University, Tirupathi for biological studies.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2476_MOESM1_ESM.docx (5.5 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • P. Asha Bhanu
    • 1
  • B. China Raju
    • 2
  • Y. Jayavardhana Rao
    • 3
  • G. Narasimha
    • 3
  • B. Kesava Rao
    • 1
    Email author
  1. 1.Department of Chemistry, University College of SciencesAcharya Nagarjuna UniversityGuntur Dt.India
  2. 2.Department of Organic Synthesis & Process ChemistryCSIR-Indian Institute of Chemical TechnologyHyderbadIndia
  3. 3.Department of VirologySri Venkateswara UniversityTirupathiIndia

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