Advertisement

Synthesis, characterization, and antioxidant activity of thymol-based paracetamol analogues

  • Pradnya S. Sathe
  • Jamatsing D. Rajput
  • Shubha S. Gunaga
  • Harun M. Patel
  • Ratnamala S. BendreEmail author
Article
  • 28 Downloads

Abstract

Thymol (2-isopropyl-5-methylphenol) is an important monoterpene phenol occurring in the essential oils isolated from Thymus vulgaris, Thymus zygis, Thymus hyemalis, etc. Thymol and its derivatives show various activities such as antioxidant, antiinflammatory, antibacterial, and antifungal effects. In the present study, a set of new benzamide derivatives (4ae), which are structurally similar to paracetamol, were synthesized from thymol using a green synthetic approach and characterized by Fourier-transform infrared (FT-IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies, liquid chromatography–mass spectrometry (LC–MS), and X-ray single-crystallographic analysis for derivative 4c. These derivatives were subjected to antioxidant testing by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and antibacterial testing against five microorganisms. Molecular docking studies of all the compounds indicated that they are good inhibitors of heme oxygenase-1. These results extend the development of thymol-based benzamide scaffolds as promising antioxidant agents.

Keywords

Benzoylation Thymol Antioxidant activity DPPH Docking Oxygenase-1 

Notes

Acknowledgements

The authors are grateful to UGC SAP (New Delhi) for providing financial assistance.

Supplementary material

11164_2019_3914_MOESM1_ESM.docx (862 kb)
Supplementary material 1 (DOCX 861 kb)

References

  1. 1.
    Z. Maksimović, M. Milenković, D. Vučićević, M. Ristić, Cent. Eur. J. Biol. 3(2), 149 (2008)Google Scholar
  2. 2.
    R.S. Bendre, J.D. Rajput, S.D. Bagul, P.S. Karandikar, Nat. Prod. Chem. Res. 4(212), 2 (2016)Google Scholar
  3. 3.
    J.D. Rajput, S.D. Bagul, S. Tadavi, R.S. Bendre, Med. Aromat. Plants (Los Angel) 5, 2167 (2016)Google Scholar
  4. 4.
    J.D. Rajput, S.D. Bagul, U.D. Pete, C.M. Zade, S.B. Padhye, R.S. Bendre, Mol. Divers. 22(1), 225 (2018)CrossRefPubMedGoogle Scholar
  5. 5.
    J.D. Rajput, S.D. Bagul, R.S. Bendre, Res. Chem. Intermed. 43(11), 6601 (2017)CrossRefGoogle Scholar
  6. 6.
    I. Karpouhtsis, E. Pardali, E. Feggou, S. Kokkini, Z.G. Scouras, P. Mavragani Tsipidou, J. Agric. Food Chem. 46(3), 1111 (1998)CrossRefGoogle Scholar
  7. 7.
    C.S. Mathela, K.K. Singh, V.K. Gupta, Acta Pol. Pharm. 67, 375 (2010)PubMedGoogle Scholar
  8. 8.
    K.P. Roda, R.N. Vansdadia, Indian J. Chem. Soc. LXV 44, 807 (1988)Google Scholar
  9. 9.
    A.T. Lupo Jr, et al., US patent no. 6,110, 888, 29 Aug (2000)Google Scholar
  10. 10.
    J.M. Desai, V.H. Shah, Indian J. Chem. B 42, 382 (2003)Google Scholar
  11. 11.
    U.D. Pete, C.M. Zade, J.D. Bhosale, S.G. Tupe, P.M. Chaudhary, A.G. Dikundwar, R.S. Bendre, Bioorg. Med. Chem. Lett. 22(17), 5550 (2016)CrossRefGoogle Scholar
  12. 12.
    H. Liang, F. Bao, X. Dong, R. Tan, C. Zhang, Q. Lu, Y. Cheng, Molecules 12(8), 1606 (2007)CrossRefPubMedPubMedCentralGoogle Scholar
  13. 13.
    B. Rojano, J. Saez, G. Schinella, J. Quijano, E. Velez, A. Gil, R. Notario, J. Mol. Struct. 877(3), 263 (2008)Google Scholar
  14. 14.
    D. Kumar, D.S. Rawat, Bioorg. Med. Chem. Lett. 23(3), 641 (2013)CrossRefPubMedGoogle Scholar
  15. 15.
    B. Tohidi, M. Rahimmalek, A. Arzani, Food Chem. 220, 153 (2017)CrossRefPubMedGoogle Scholar
  16. 16.
    S. Kumari, R.V. Kumaraswamy, R.C. Choudhary, S.S. Sharma, A. Pal, R. Raliya, V. Saharan, Sci. Rep., 8 (2018)Google Scholar
  17. 17.
    S. Tyagarajan, P.K. Chakravarty, Tetrahedron Lett. 46, 7889 (2005)CrossRefGoogle Scholar
  18. 18.
    D.B. Suresh, D.R. Jamatsing, S.K. Pravin, S.B. Ratnamala, Mod. Chem. Appl. 4, 193 (2016).Google Scholar
  19. 19.
    J.D. Rajput, S.D. Bagul, R.S. Bendre, Res. Chem. Intermed. 43(8), 4893 (2017)CrossRefGoogle Scholar
  20. 20.
    M.A. Alisi, M. Brufani, N. Cazzolla, F. Ceccacci, P. Dragone, M. Felici, G. Furlotti, B. Garofalo, A. La Bella, O. Lanzalunga, F. Leonelli, Tetrahedron 68(49), 10180 (2012)CrossRefGoogle Scholar
  21. 21.
    S.B. Nimse, D. Pal, RSC Adv. 5(35), 27986 (2015)CrossRefGoogle Scholar
  22. 22.
    R.S. Borges, T.G. Barros, G.A. Pereira, J. Batista Jr., R.F. Beleza Filho, A.A. Veiga, C.A. Barros, Pharmacol. Pharma. 5(13), 1185 (2014)CrossRefGoogle Scholar
  23. 23.
    V.Z. Mota, G.S. de Carvalho, P.P. Corbi, F.R. Bergamini, A.L. Formiga, R. Diniz, A. Cuin, Spectrochim. Acta A 99, 110 (2012)CrossRefGoogle Scholar
  24. 24.
    M.J. Rodríguez-Doutón, Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry (Taylor and Francis, Abingdon, 2006), p. 655Google Scholar
  25. 25.
    B.S. Vashi, D.S. Mehta, V.H. Shah, Indian J. Chem. Sec. B 4, 802 (1995)Google Scholar
  26. 26.
    L.V.G. Nargund, G.R.N. Reddy, V. Hari Prasad, Ind. J. Chem. Sect. B Organic 35, 499 (1996)Google Scholar
  27. 27.
    S. Ghosh, J. Das, Organic. Chem. Int. (2010).Google Scholar
  28. 28.
    E. Bendary, R.R. Francis, H.M.G. Ali, M.I. Sarwat, S. El Hady, Ann. Agric. Sci. 58, 173 (2013)CrossRefGoogle Scholar
  29. 29.
    J.H. Jorgensen, E.M.P. Turnidge, E.J. Baron, M.L. Landry, M.A. Pfaller, Manual of Clinical Microbiology (Taylor and Francis, Washington, DC, 2007), p. 1152Google Scholar
  30. 30.
    J.H. Jorgensen, M.L. Landry, M.A. Pfaller, Manual of Clinical Microbiology (Taylor and Francis, Washington, DC, 2007), p. 1972Google Scholar
  31. 31.
    M.N. Rahman, J.Z. Vlahakis, W.A. Szarek, K. Nakatsu, Z. Jia, J. Med. Chem. 51, 5943 (2008)CrossRefPubMedGoogle Scholar
  32. 32.
    M.N. Rahman, D. Vukomanovic, J.Z. Vlahakis, W.A. Szarek, K. Nakatsu, Z. Jia, J. R. Soc. Interface 10(78), 20120697 (2013)CrossRefPubMedPubMedCentralGoogle Scholar
  33. 33.
    A. Carletta, A. Tilborg, L. Moineaux, J. de Ruyck, L. Basile, L. Salerno, S. Guccione, Acta Cryst. B Cryst. Eng. Mater. 71(4), 447 (2015)CrossRefGoogle Scholar
  34. 34.
    M.C.I. Ienaşcu, N.S. Mariana, T. Cristian, M.P. Iuliana, C. Adina, 2015 E-Health and Bioengineering Conference (EHB) (IEEE, 2015), p. 1Google Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Pradnya S. Sathe
    • 1
  • Jamatsing D. Rajput
    • 1
  • Shubha S. Gunaga
    • 2
  • Harun M. Patel
    • 3
  • Ratnamala S. Bendre
    • 1
    Email author
  1. 1.Department of Pesticides and Agrochemicals, School of Chemical SciencesKavayitri Bahinabai Chaudhari North Maharashtra UniversityJalgaonIndia
  2. 2.Solid State and Structural Chemistry UnitIndian Institute of ScienceBangaloreIndia
  3. 3.Division of Computer Aided Drug Design, Department of Pharmaceutical ChemistryR. C. Patel Institute of Pharmaceutical Education and ResearchShirpur (Dhule)India

Personalised recommendations