Issue

Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Creative Commons License

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

Synthesis, Characterization, PASS Prediction and in silico ADME Studies of Ester and Ether Linked 1,4-Disubstituted 1,2,3-Triazoles Derivatives via Click Approach

https://doi.org/10.14233/ajchem.2020.22748%20
G. Krishnaswamy
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
P. Raghuram Shetty
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
https://orcid.org/0000-0003-0234-5662
B. Roopa
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
Salma Banu
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
H.J. Preritha
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
B.S. Rajeshwari
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
M. Ravikumar
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
K. Pruthviraj
https://orcid.org/0000-0002-1167-3783
D.B. Aruna Kumar
Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India
S. Sreenivasa
1 Department of Studies and Research in Organic Chemistry, Tumkur University, Tumakuru-572103, India 2 Deputy Adviser, National Assessment and Accreditation Council, Nagarbhavi, Bengaluru-560072, India
https://orcid.org/0000-0003-1096-5837

Corresponding Author(s) : S. Sreenivasa

drsreenivasa@yahoo.co.in

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Abstract

In the present investigation, we focused our interest on the synthesis of pharmacophoric units (quinoline and 1,2,3-triazole) linked through ester (3a-b) and (substituted aromatic ring and 1,2,3-triazole) linked through an ether (3c-h). The synthesis involves multiple sequence of reactions viz. diazotization reaction followed by nucleophilic substitution and finally Cu(I)-catalyzed alkyne azide cycloaddition reaction (CuAAC). The assigned structures of the compound were confirmed by 1H & 13C NMR and mass spectrometry. Prediction of activity spectra or substances (PASS) training set for the synthesized compounds were carried out using PASS software. Interestingly, PASS prediction of the compounds (3a-h) showed that the compounds  are more potent as anti-inflammatory (Pa < 0.65) compared to antibacterial (Pa < 0.33) as well as antifungal agents (Pa < 0.35). Furthermore, these compounds were subjected to in silico  ADMETox evaluation. All the compounds were found to pass the ADME evaluation and only few compounds passed the predicted toxicity evaluation. This work could be used as an initial approach in identifying potential novel molecules with promising activity and low toxicity.

Keywords

1,2,3-Triazole 1,3-Dipolar cycloaddition Aromatic Azides Prediction of activity spectra for substances Druglikeness
Krishnaswamy, G. ., Shetty, P. R. ., Roopa, B. ., Banu, S. ., Preritha, H. ., Rajeshwari, B. ., … Sreenivasa, S. . (2020). Synthesis, Characterization, PASS Prediction and in silico ADME Studies of Ester and Ether Linked 1,4-Disubstituted 1,2,3-Triazoles Derivatives via Click Approach. Asian Journal of Chemistry, 32(8), 1857–1864. https://doi.org/10.14233/ajchem.2020.22748
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. R. Reddyrajula and U. Dalimba, ChemistrySelect, 4, 2685 (2019); https://doi.org/10.1002/slct.201803946
  2. A. Ayati, S. Emami and A. Foroumadi, Eur. J. Med. Chem., 109, 380 (2016); https://doi.org/10.1016/j.ejmech.2016.01.009
  3. I. Briguglio, S. Piras, P. Corona, E. Gavini, M. Nieddu, G. Boatto and A. Carta, Eur. J. Med. Chem., 97, 612 (2015); https://doi.org/10.1016/j.ejmech.2014.09.089
  4. K.R.A. Abdellatif and R.B. Bakr, Bioorg. Chem., 78, 341 (2018); https://doi.org/10.1016/j.bioorg.2018.03.032
  5. R.J. Herr, Bioorg. Med. Chem., 10, 3379 (2002); https://doi.org/10.1016/S0968-0896(02)00239-0
  6. L. Dymiñska, Bioorg. Med. Chem., 23, 6087 (2015); https://doi.org/10.1016/j.bmc.2015.07.045
  7. J.A. Maertens, Clin. Microbiol. Infect., 10, 1 (2004); https://doi.org/10.1111/j.1470-9465.2004.00841.x
  8. F.D.C. Da Silva, M.C.B.V. De Souza, I.I.P. Frugulhetti, H.C. Castro, S.L.D.O. Souza, T.M.L. De Souza, D.Q. Rodrigues, A.M.T. Souza, P.A. Abreu, F. Passamani, C.R. Rodrigues and V.F. Ferreira, Eur. J. Med. Chem., 44, 373 (2009); https://doi.org/10.1016/j.ejmech.2008.02.047
  9. M.J. Giffin, H. Heaslet, A. Brik, Y.C. Lin, G. Cauvi, C.-H. Wong, D.E. McRee, J.H. Elder, C.D. Stout and B.E. Torbett, J. Med. Chem., 51, 6263 (2008); https://doi.org/10.1021/jm800149m
  10. S. Cocklin, H. Gopi, B. Querido, M. Nimmagadda, S. Kuriakose, C. Cicala, S. Ajith, S. Baxter, J. Arthos, J. Martin-Garcia and I.M. Chaiken, J. Virol., 81, 3645 (2007); https://doi.org/10.1128/JVI.01778-06
  11. A. Brik, J. Alexandratos, Y.C. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, D.S. Goodsell and C.-H. Wong, ChemBioChem, 6, 1167 (2005); https://doi.org/10.1002/cbic.200500101
  12. W.J. Yu, Q. Rao, M. Wang, Z. Tian, D. Lin, X.R. Liu and J.X. Wang, Leuk. Res., 30, 575 (2006); https://doi.org/10.1016/j.leukres.2005.08.028
  13. L.B. Peterson and B.S.J. Blagg, Bioorg. Med. Chem. Lett., 20, 3957 (2010); https://doi.org/10.1016/j.bmcl.2010.04.140
  14. M. Nahrwold, T. Bogner, S. Eissler, S. Verma and N. Sewald, Org. Lett., 12, 1064 (2010); https://doi.org/10.1021/ol1000473
  15. J. Doiron, A.H. Soultan, R. Richard, M.M. Toure, N. Picot, R. Richard, M. Cuperlovic-Culf, G.A. Robichaud and M. Touaibia, Eur. J. Med. Chem., 46, 4010 (2011); https://doi.org/10.1016/j.ejmech.2011.05.074
  16. I. Fichtali, M. Chraibi, F.E. Aroussi, A. Ben-Tama, E. M. E. Hadrami, K. F. Benbrahim and S. E. Stiriba, Der. Pharm. Chem., 8, 236 (2016).
  17. B. F. Abdel-Wahab, H. A. Mohamed and G. E. A. Awad, Eur. Chem. Bull., 4, 106 (2015).
  18. D. Dheer, V. Singh and R. Shankar, Bioorg. Chem., 71, 30 (2017); https://doi.org/10.1016/j.bioorg.2017.01.010
  19. T.F. Borgati, R.B. Alves, R.R. Teixeira, P.F. Rossimiriam, T.G. Perdigão, S.F. Silva, A.A. Santos and A.J.O. Bastidas, J. Braz. Chem. Soc., 24, 953 (2013); https://doi.org/10.5935/0103-5053.20130121
  20. R.A. Silva, E.D. Quintela, G.M. Mascarin, J.A.F. Barrigossi and L.M. Lião, Sci. Agric., 70, 152 (2013); https://doi.org/10.1590/S0103-90162013000300003
  21. Q. Ma, S. Qi, X. He, Y. Tang and G. Lu, Corros. Sci., 129, 91 (2017); https://doi.org/10.1016/j.corsci.2017.09.025
  22. L. Wang, M.J. Zhu, F.C. Yang and C.W. Gao, Int. J. Corros., 2012, 573964 (2012); https://doi.org/10.1155/2012/573964
  23. T.Y.B. Leung, M. Kang, B.F. Corry and A.A. Gewirth, J. Electrochem. Soc., 147, 3326 (2000); https://doi.org/10.1149/1.1393902
  24. K.S. McNeill and D.A. Cancilla, Bull. Environ. Contam. Toxicol., 82, 265 (2009); https://doi.org/10.1007/s00128-008-9626-z
  25. B. Schulze and U.S. Schubert, Chem. Soc. Rev., 43, 2522 (2014); https://doi.org/10.1039/c3cs60386e
  26. Y. Hua and A.H. Flood, Chem. Soc. Rev., 39, 1262 (2010); https://doi.org/10.1039/b818033b
  27. M. Arseneault, C. Wafer and J.F. Morin, Molecules, 20, 9263 (2015); https://doi.org/10.3390/molecules20059263
  28. D. Astruc, L. Liang, A. Rapakousiou and J. Ruiz, Acc. Chem. Res., 45, 630 (2012); https://doi.org/10.1021/ar200235m
  29. D. Srividhya, S. Manjunathan, S. Thirumaran, C. Saravanan and S. Senthil, J. Mol. Struct., 927, 7 (2009); https://doi.org/10.1016/j.molstruc.2009.01.035
  30. H. Gallardo, F. Ely, A. Bortoluzzi and G. Conte, Liq. Cryst., 32, 667 (2005); https://doi.org/10.1080/02678290500139732
  31. N.A. Evans, Aust. J. Chem., 34, 691 (1981); https://doi.org/10.1071/CH9810691
  32. P. M. Miladinova and T. N. Konstantinova, J. Chem. Tech. Metall., 50, 229 (2015).
  33. K.M. Rajalekshmi, C.A. Jaleel, M.M. Azooz and R. Panneerselvam, Adv. Biol. Res., 3, 117 (2009).
  34. I.A. Khalil, E.I. Mercer and Z.X. Wang, Plant Sci., 66, 21 (1990); https://doi.org/10.1016/0168-9452(90)90164-J
  35. K. Uzun, E. Cevik and M. Senel, Am. J. Chem, 1, 16 (2012); https://doi.org/10.5923/j.chemistry.20110101.03
  36. G. Zhang, Y. Wang, X. Wen, C. Ding and Y. Li, Chem. Commun., 48, 2979 (2012); https://doi.org/10.1039/c2cc18023e
  37. B. Garudachari, A.M. Isloor, M.N. Satyanarayana, H.K. Fun and G. Hegde, Eur. J. Med. Chem., 74, 324 (2014); https://doi.org/10.1016/j.ejmech.2014.01.008
  38. K.K. Kumar, S.P. Seenivasan, V. Kumar and T.M. Das, Carbohydr. Res., 346, 2084 (2011); https://doi.org/10.1016/j.carres.2011.06.028
  39. K.D. Thomas, A.V. Adhikari, I.H. Chowdhury, E. Sumesh and N.K. Pal, Eur. J. Med. Chem., 46, 2503 (2011); https://doi.org/10.1016/j.ejmech.2011.03.039
  40. M.J. Khoshkholgh, S. Balalaie, R. Gleiter and F. Rominger, Tetrahedron, 64, 10924 (2008); https://doi.org/10.1016/j.tet.2008.08.056
  41. V. Poroikov, D. Filimonov, A. Lagunin, T. Gloriozova and A. Zakharov, SAR QSAR Environ. Res., 18, 101 (2007); https://doi.org/10.1080/10629360601054032
  42. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
  43. P. Banerjee, A.O. Eckert, A.K. Schrey and R. Preissner, Nucleic Acids Res., 46(W1), W257 (2018); https://doi.org/10.1093/nar/gky318
  44. R.B. van Breemen and Y. Li, Expert Opin. Drug Metab. Toxicol.,, 1, 175 (2005); https://doi.org/10.1517/17425255.1.2.175
  45. S. Alam and F. Khan, Sci. Rep., 8, 5524 (2018); https://doi.org/10.1038/s41598-018-23768-7
  46. M.N. Drwal, P. Banerjee, M. Dunkel, M.R. Wettig and R. Preissner, Nucleic Acids Res., 42(W1), W53 (2014); https://doi.org/10.1093/nar/gku401
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 6