Issue

Vol. 35 No. 1 (2023): Vol 35 Issue 1

Copyright (c) 2023 AJC

Creative Commons License

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

1,2,3-Triazoles containing Thiazole-Piperazine Moieties: Synthesis, Biological Assessment and Molecular Docking

https://doi.org/10.14233/ajchem.2023.26904
Krishna Chaitanya Veeranki
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500085, India ; Chemveda Life Sciences Pvt Ltd., IDA Uppal Hyderabad-500039, India
Jalapathi Pochampally
Department of Chemistry, Osmania University, Hyderabad-500007, India
Ravi Chander Maroju
Department of Chemistry, Mahatma Gandhi Institute of Technology, Hyderabad-500075, India
Vishnu Thumma
Department of Sciences and Humanities, Matrusri Engineering College, Hyderabad-500059, India
Lakshmi Satya Boddu
Department of Pharmaceutics, Vishnu Institute of Pharmaceutical Education and Research, Medak-502313, India

Corresponding Author(s) : Jalapathi Pochampally

pochampalli.ou.chemi@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 1 (2023): Vol 35 Issue 1

Abstract

A novel series of thiazole-triazole-piperazine multi hybrids was designed for antimicrobial activity and the synthetic method for this series has been developed by copper catalyzed 1,3-dipolar cycloaddition of thiazole-based azide with Boc-piperidine based alkyne in the presence of CuSO4 and sodium ascorbate. Boc deprotection followed by alkylation of piperidine moiety in hybrid derivatives was also carried out. All the target compounds were confirmed using FTIR, 1H NMR, 13C NMR and LC-MS spectral techniques. These compounds were screened for the antimicrobial activity against bacteria and fungi. The antimicrobial activities are also comparable to standard drugs ampicillin and clotrimazole. All the molecules showed good to moderate activity and supported by molecular docking studies and ADME prediction.

Keywords

Thiazole Piperazine Antimicrobial Molecular docking 1,2,3-Triazole
Chaitanya Veeranki, K., Pochampally, J., Chander Maroju, R., Thumma, V., & Satya Boddu, L. (2022). 1,2,3-Triazoles containing Thiazole-Piperazine Moieties: Synthesis, Biological Assessment and Molecular Docking. Asian Journal of Chemistry, 35(1), 125–134. https://doi.org/10.14233/ajchem.2023.26904
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M. Gümüs, M. Yakan and I. Koca, Future Med. Chem., 11, 1979 (2019); https://doi.org/10.4155/fmc-2018-0196
  2. R. Mishra, P.K. Sharma, P.K. Verma, I. Tomer, G. Mathur and P.K. Dhakad, J. Heterocycl. Chem., 54, 2103 (2017); https://doi.org/10.1002/jhet.2827
  3. M. T. Chhabria, S. Patel, P. Modi and P. S. Brahmkshatriya, Curr. Top. Med. Chem., 16, 2841 (2016); https://doi.org/10.2174/1568026616666160506130731
  4. N. Ergenç, G. Çapan, N.S. Günay, S. Özkirimli, M. Güngör, S. Özbey and E. Kendi, Arch. Pharm., 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AIDARDP343>3.0.CO;2-0
  5. K. Tsuji and H. Ishikawa, Bioorg. Med. Chem. Lett., 4, 1601 (1994); https://doi.org/10.1016/S0960-894X(01)80574-6
  6. A.S. Cantrell, P. Engelhardt, M. Högberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, J. Kangasmetsä, M.D. Kinnick, P. Lind, J.M. Morin, M.A. Muesing, R. Noreén, B. Öberg, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West and H. Zhang, J. Med. Chem., 39, 4261 (1996); https://doi.org/10.1021/jm950639r
  7. P.C. Sharma, K.K. Bansal, A. Sharma, D. Sharma and A. Deep, Eur. J. Med. Chem., 188, 112016 (2020); https://doi.org/10.1016/j.ejmech.2019.112016
  8. B.F. Abdel-Wahab, E. Abdel-Latif, H.A. Mohamed and G.E.A. Awad, Eur. J. Med. Chem., 52, 263 (2012); https://doi.org/10.1016/j.ejmech.2012.03.023
  9. M. Nagamani, T. Vishnu, P. Jalapathi and M. Srinivas, J. Indian Chem. Soc., 19, 1049 (2022); https://doi.org/10.1007/s13738-021-02365-y
  10. K.K. Angajala, S. Vianala, R. Macha, M. Raghavender, M.K. Thupurani and P.J. Pathi, Springerplus, 5, 423 (2016); https://doi.org/10.1186/s40064-016-2052-5
  11. M. Raghavender, A.K. Kumar, V. Sunitha, T. Vishnu and P. Jalapathi, Russ. J. Gen. Chem., 90, 697 (2020); https://doi.org/10.1134/S1070363220040210
  12. D. Veeranna, L. Ramdas, G. Ravi, V. Thumma, S. Bujji and J. Ramchander, ChemistrySelect, 7, e202201758 (2022); https://doi.org/10.1002/slct.202201758
  13. G. Kaur and R. Singh, Int. J. Pharm. Pharm. Sci., 6, 35 (2014).
  14. C.-Y. Cheng, A. Haque, M.-F. Hsieh, S. Imran Hassan, M.S.H. Faizi, N. Dege and M.S. Khan, Int. J. Mol. Sci., 21, 3823 (2020); https://doi.org/10.3390/ijms21113823
  15. Y. Tian, Z. Liu, J. Liu, B. Huang, D. Kang, H. Zhang, E. De Clercq, D. Daelemans, C. Pannecouque, K.H. Lee, C.H. Chen, P. Zhan and X. Liu, Eur. J. Med. Chem., 151, 339 (2018); https://doi.org/10.1016/j.ejmech.2018.03.059
  16. S. Sathish Kumar and H. P. Kavitha, Mini Rev. Org. Chem., 10, 40 (2013); https://doi.org/10.2174/1570193X11310010004
  17. S. Sharma, M.K. Gupta, A.K. Saxena and P.M.S. Bedi, Bioorg. Med. Chem., 23, 7165 (2015); https://doi.org/10.1016/j.bmc.2015.10.013
  18. H. Singh, M. Kumar, K. Nepali, M.K. Gupta, A.K. Saxena, S. Sharma and P.M.S. Bedi, Eur. J. Med. Chem., 116, 102 (2016); https://doi.org/10.1016/j.ejmech.2016.03.050
  19. H.R. Suryavanshi and M.M. Rathore, Org. Commun., 10, 228 (2017); https://doi.org/10.25135/acg.oc.23.17.05.026
  20. A. Khalaj, N. Adibpour, A.R. Shahverdi and M. Daneshtalab, Eur. J. Med. Chem., 39, 699 (2004); https://doi.org/10.1016/j.ejmech.2004.04.004
  21. R.S. Upadhayaya, N. Sinha, S. Jain, N. Kishore, R. Chandra and S.K. Arora, Bioorg. Med. Chem., 12, 2225 (2004); https://doi.org/10.1016/j.bmc.2004.02.014
  22. P. Chaudhary, R. Kumar, A.K. Verma, D. Singh, V. Yadav, A.K. Chhillar, G.L. Sharma and R. Chandra, Bioorg. Med. Chem., 14, 1819 (2006); https://doi.org/10.1016/j.bmc.2005.10.032
  23. C.L.E. Broekkamp, D. Leysen, B.W.M.M. Peeters and R.M. Pinder, J. Med. Chem., 38, 4615 (1995); https://doi.org/10.1021/jm00023a001
  24. H. Naito, S. Ohsuki, R. Atsumi, M. Minami, M. Mochizuki, K. Hirotani, E. Kumazawa and A. Ejima, Chem. Pharm. Bull. (Tokyo), 53, 153 (2005); https://doi.org/10.1248/cpb.53.153
  25. M. Ibarra, E. Hong and R. VillalobosMolina, J. Auton. Pharmacol., 20, 139 (2000); https://doi.org/10.1046/j.1365-2680.2000.00172.x
  26. J. Yoon, E.A. Yoo, J.Y. Kim, A.N. Pae, H. Rhim, W.K. Park, J.Y. Kong and H.Y. Park Choo, Bioorg. Med. Chem., 16, 5405 (2008); https://doi.org/10.1016/j.bmc.2008.04.023
  27. G.D. Tollefson, S.P. Lancaster and J. Montague-Clouse, Psychopharmacol. Bull., 27, 163 (1991).
  28. S. Rotzinger, J. Fang and G.B. Baker, Drug Metab. Dispos., 26, 572 (1998).
  29. K. Walayat, N.A. Mohsin, S. Aslam and M. Ahmad, Turkish J. Chem., 43, 1 (2019); https://doi.org/10.3906/kim-1806-7
  30. D. Dias-da-Silva, M.D. Arbo, M.J. Valente, M.L. Bastos and H. Carmo, Toxicol. in vitro, 29, 987 (2015); https://doi.org/10.1016/j.tiv.2015.04.001
  31. G.C. Moraski, N. Deboosère, K.L. Marshall, A. Vandeputte, C. Hastings, H.A. Weaver, L. Woolhiser, A.J. Lenaerts, P. Brodin and M.J. Miller, PLoS One, 15, e0227224 (2020); https://doi.org/10.1371/journal.pone.0227224
  32. J.B. Wan, Q.W. Zhang, S.J. Hong, P. Li, S.P. Li and Y.T. Wang, Molecules, 17, 5836 (2012); https://doi.org/10.3390/molecules17055836
  33. K.N. Ankali, J. Rangaswamy, M. Shalavadi, G. Krishnamurthy and , N. Naik, J. Mol. Struct., 1236, 130357 (2021); https://doi.org/10.1016/j.molstruc.2021.130357
  34. R.S. Gokhale, D.S. Reddy, B. Seetharamsingh, P. Ganju and V.T. Natarajan, Novel 1,2,3-Triazole-Thiazole Compounds, Process for Preparation and Use Thereof, US Patent US20180370962A1 (2019).
  35. A. Alsayari, A.B. Muhsinah, Y.I. Asiri, F.A. Al-aizari, N.A. Kheder, Z.M. Almarhoon, H.A. Ghabbour and Y.N. Mabkhot, Molecules, 26, 5383 (2021); https://doi.org/10.3390/molecules26175383
  36. T. Yakantham, R. Sreenivasulu, G. Alluraiah, M.B. Tej and R. Ramesh Raju, Russ. J. Gen. Chem., 89, 2522 (2019); https://doi.org/10.1134/S1070363219120314
  37. S. Anil Kumar, S. Madderla, R. Dharavath, N. Nalaparaju, R. Katta, S. Gundu, V. Thumma, B. Prashanth and D. Ashok, J. Heterocycl. Chem., 59, 1180 (2022); https://doi.org/10.1002/jhet.4458
  38. S. Dallakyan and A.J. Olson, Small Molecule Library Screening by Docking with PyRx, In: Methods in Molecular Biology, Springer, pp. 243-250 (2015);
  39. O. Trott and A.J. Olson, J. Comput. Chem., 31, NA (2009); https://doi.org/10.1002/jcc.21334
  40. S. Mouilleron, M.A. Badet-Denisot and B. Golinelli-Pimpaneau, J. Mol. Biol., 377, 1174 (2008); https://doi.org/10.1016/j.jmb.2008.01.077
  41. V. Ragunathan, M.Tech. Thesis, Computational Approach Towards Targeting Candidapepsin of Candida albicans against oral candidiasis, (2021).
  42. C. Borelli, E. Ruge, J.H. Lee, M. Schaller, A. Vogelsang, M. Monod, H.C. Korting, R. Huber and K. Maskos, Proteins, 72, 1308 (2008); https://doi.org/10.1002/prot.22021
  43. A. Teplyakov, G. Obmolova, B. Badet and M.A. Badet-Denisot, J. Mol. Biol., 313, 1093 (2001); https://doi.org/10.1006/jmbi.2001.5094
  44. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 1 (2017); https://doi.org/10.1038/srep42717
  45. C.A. Lipinski, Drug Discov. Today. Technol., 1, 337 (2004); https://doi.org/10.1016/j.ddtec.2004.11.007
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0