Issue

Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Laccase Enzyme Catalyst Mediated Synthesis of Pyrimidines and its Antibacterial, Antifungal, Molecular Docking Studies

https://doi.org/10.14233/ajchem.2022.23843
K. Shenbagam
Department of Chemistry, Cauvery College for Women, Thiruchirappalli-620018, India
G. Sivasankari
Department of Chemistry, Cauvery College for Women, Thiruchirappalli-620018, India

Corresponding Author(s) : K. Shenbagam

suthanp2020@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

Abstract

The novel synthesis of pyrimidine derivatives (1a-f) by using green chemistry technique with laccase as an enzyme catalyst. FT-IR, 1H NMR, and elemental analyses were used to describe the produced compounds (1a-f). Antibacterial, antifungal, and molecular docking investigations to characterize the produced pyrimidine derivatives (1a-f). In antibacterial testing, compound 1e, showed considerable action towards E. coli (MIC 02 μg/mL) as associated to ciprofloxacin (MIC 04 μg/mL). When related to clotrimazole in antifungal assessment, compound 1d was shown to be significant activity towards C. albicans (MIC 0.25 μg/mL) than clotrimazole (MIC 0.5 μg/mL). Molecular docking experiments further indicate that compound 1e inhibited antibacterial and compound 1d inhibited antifungal proteins more effectively than the control compounds ciprofloxacin and clotrimazole.

Keywords

Pyrimidine Enzyme catalyst Green chemistry Antibacterial activity Antifungal activity Molecular docking
Shenbagam, K., & Sivasankari, G. (2022). Laccase Enzyme Catalyst Mediated Synthesis of Pyrimidines and its Antibacterial, Antifungal, Molecular Docking Studies. Asian Journal of Chemistry, 34(8), 2105–2112. https://doi.org/10.14233/ajchem.2022.23843
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. S.E. John, S. Gulati and N. Shankaraiah, Org. Chem. Front., 8, 4237 (2021); https://doi.org/10.1039/D0QO01480J
  2. C.S. Graebin, F.V. Ribeiro, K.R. Rogério and A.E. Kümmerle, Curr. Org. Synth., 16, 855 (2019); https://doi.org/10.2174/1570179416666190718153703
  3. R.O. Rocha, M.O. Rodrigues and B.A.D. Neto, ACS Omega, 5, 972 (2020); https://doi.org/10.1021/acsomega.9b03684
  4. C. Cimarelli, Molecules, 24, 2372 (2019); https://doi.org/10.3390/molecules24132372
  5. P.G. Cozzi and E. Rivalta, Angew. Chem. Int. Ed., 44, 3600 (2005); https://doi.org/10.1002/anie.200462757
  6. T. Zarganes-Tzitzikas, A.L. Chandgude and A. Dömling, The Chem. Record, 15, 981 (2015); https://doi.org/10.1002/tcr.201500201
  7. C.K. Jadhav, A.S. Nipate, A.V. Chate, V.D. Songire, A.P. Patil and C.H. Gill, ACS Omega, 4, 22313 (2019); https://doi.org/10.1021/acsomega.9b02286
  8. B.R. Prashantha Kumar, G. Sankar, S. Chandrashekaran and R.B. Nasir Baig, Eur. J. Med. Chem., 44, 4192 (2009); https://doi.org/10.1016/j.ejmech.2009.05.014
  9. T. Matsuda and I. Hirao, Nippon Kagaku Zasshi, 86, 1195 (1965).
  10. Y.S. Sadanandam, M.M. Shetty and P.V. Diwan, Eur. J. Med. Chem., 27, 87 (1992); https://doi.org/10.1016/0223-5234(92)90066-A
  11. E.W. Hurst and R.I. Hull, J. Med. Pharm. Chem., 3, 215 (1961); https://doi.org/10.1021/jm50015a002
  12. M. Kurono, M. Hayashi, K. Miura, Y. Isogawa and K. Sawai, JP Patent 62,267,272 (1987).
  13. C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.V.N. Reddy, Tetrahedron Lett., 43, 2657 (2002); https://doi.org/10.1016/S0040-4039(02)00280-0
  14. Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000); https://doi.org/10.1021/jo9919052
  15. W. Su, J. Li, Z. Zheng and Y. Shen, Tetrahedron Lett., 46, 6037 (2005); https://doi.org/10.1016/j.tetlet.2005.07.021
  16. X. Chen and Y. Peng, Catal. Lett., 122, 310 (2008); https://doi.org/10.1007/s10562-007-9377-1
  17. J. Lu and H. Ma, Synlett, 63 (2000); https://doi.org/10.1055/s-2000-6469
  18. A.S. Paraskar, G.K. Dewkar and A. Sudalai, Tetrahedron Lett., 44, 3305 (2003); https://doi.org/10.1016/S0040-4039(03)00619-1
  19. N.Y. Fu, Y.E. Yuan, Z. Cao, S.W. Wang, J.T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); https://doi.org/10.1016/S0040-4020(02)00455-6
  20. H. Salehi and Q.-X. Guo, Synth. Commun., 34, 171 (2004); https://doi.org/10.1081/SCC-120027250
  21. E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); https://doi.org/10.1021/jo970846u
  22. S.L. Jain, J.K. Joseph and B. Sain, Catal. Lett., 115, 52 (2007); https://doi.org/10.1007/s10562-007-9070-4
  23. Q. Sun, Y. Wang, Z. Ge, T. Cheng and R. Li, Synthesis, 1047 (2004); https://doi.org/10.1055/s-2004-822331
  24. R. Ghosh, S. Maiti and A. Chakraborty, J. Mol. Catal. Chem., 217, 47 (2004); https://doi.org/10.1016/j.molcata.2004.02.025
  25. P.G. Mandhane, R.S. Joshi, D.R. Nagargoje and C.H. Gill, Tetrahedron Lett., 51, 3138 (2010); https://doi.org/10.1016/j.tetlet.2010.04.037
  26. M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc., Perkin Trans. 1, 1845 (2002); https://doi.org/10.1039/B205539M
  27. M. López-Iglesias and V. Gotor-Fernández, Chem. Rec., 15, 743 (2015); https://doi.org/10.1002/tcr.201500008
  28. L. Forti, M.R. Cramarossa, S. Filippucci, G. Tasselli, B. Turchetti and P. Buzzini, Academic Press: Cambridge, MA, USA, p. 187 (2018).
  29. E.M. Sulman, V.G. Matveeva and L.M. Bronstein, Curr. Opin. Chem. Eng., 26, 1 (2019); https://doi.org/10.1016/j.coche.2019.06.005
  30. U.T. Bornscheuer and R.J. Kazlauskas, Angew. Chem. Int. Ed., 43, 6032 (2004); https://doi.org/10.1002/anie.200460416
  31. K. Hult and P. Berglund, Trends Biotechnol., 25, 231 (2007); https://doi.org/10.1016/j.tibtech.2007.03.002
  32. M. Svedendahl, K. Hult and P. Berglund, J. Am. Chem. Soc., 127, 17988 (2005); https://doi.org/10.1021/ja056660r
  33. Y. Terao, K. Miyamoto and H. Ohta, Chem. Lett., 36, 420 (2007); https://doi.org/10.1246/cl.2007.420
  34. A.W. Bauer, W.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
  35. R.G. Petersdorf and J.C. Sherris, Am. J. Med., 39, 766 (1965); https://doi.org/10.1016/0002-9343(65)90096-3
  36. A.H. Collins, Microbiological Methods, Butterworth: London, Ed.: 2 (1976).
  37. S.H. Gillespie, Medical Microbiology-Illustrated, Butterworth: Heinemann, London, p. 234 (1994).
  38. O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
  39. A.A. Abdel-Aziz, Y.A. Asiri and M.H. Al-Agamy, Eur. J. Med. Chem., 46, 5487 (2011); https://doi.org/10.1016/j.ejmech.2011.09.011
  40. V. Singh, V. Praveen, D. Tripathi, S. Haque, P. Somvanshi, S. Katti and C. Tripathi, Sci. Rep., 5, 11948 (2015); https://doi.org/10.1038/srep11948
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 1