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Research on Chemical Intermediates

, Volume 45, Issue 10, pp 5159–5182 | Cite as

New 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives: Facile synthesis, biological evaluation and molecular docking study

  • Smita P. Khare
  • Tejshri R. Deshmukh
  • Satish V. Akolkar
  • Jaiprakash N. Sangshetti
  • Vijay M. Khedkar
  • Bapurao B. ShingateEmail author
Article
  • 97 Downloads

Abstract

An efficient ultrasound-promoted one-pot three-component synthesis of a series of new 1,2,3-triazole-linked tetrahydrobenzo[b]pyran derivatives as antifungal and antioxidant agents using NaHCO3 has been described for the first time. The bioassay result indicates that the compounds 7b, 7c, 7i and 7j displayed excellent antifungal activity with lower MIC = 12.5 µg/mL than the reference drug miconazole. Most of the compounds from the series showed promising antioxidant activity with lower IC50 values in the range 12.47 ± 0.60–16.49 ± 0.44 µg/mL in comparison with butylated hydroxy toluene (BHT). Molecular docking studies revealed that most of the newly synthesized compounds showed excellent binding affinity with the potential target sterol 14α-demethylase (CYP51). Moreover, in silico adsorption, distribution, metabolism and excretion (ADME) study shows that the derivatives may possess drug like properties for further development of newer therapeutic agents.

Graphic abstract

Keywords

1,2,3-Triazole Tetrahydrobenzo[b]pyran Multicomponent reactions Antifungal activity Molecular docking study 

Notes

Acknowledgements

One of the authors, S.P.K., is grateful to Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, for the award of university scholars fellowship. The authors are also thankful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431 004, India, for providing the laboratory facility. The authors are also thankful to Schrodinger Inc. for providing the Schrodinger molecular modeling software for performing the molecular studies.

Supplementary material

11164_2019_3906_MOESM1_ESM.pdf (3.1 mb)
Supplementary material 1 (PDF 3153 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Smita P. Khare
    • 1
  • Tejshri R. Deshmukh
    • 1
  • Satish V. Akolkar
    • 1
  • Jaiprakash N. Sangshetti
    • 2
  • Vijay M. Khedkar
    • 3
  • Bapurao B. Shingate
    • 1
    Email author
  1. 1.Department of ChemistryDr. Babasaheb Ambedkar Marathwada UniversityAurangabadIndia
  2. 2.Department of Pharmaceutical ChemistryY. B. Chavan College of PharmacyAurangabadIndia
  3. 3.Department of Pharmaceutical ChemistryShri Vile Parle Kelavani Mandal’s Institute of PharmacyDhuleIndia

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