Issue

Vol. 38 No. 5 (2026): Vol 38, Issue 5, 2026

Copyright (c) 2026 Potharaju Sunil Kumar, Rambabu Bhukya, Chandulal Bhukya, Nampally Rajitha, Goli J. Rupasree, Nalaparaju Nagaraju, Ramchander Jadhav

Creative Commons License

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

Design and Synthesis of Novel Hydrazone-Linked 1,2,3-Triazole-Pyrazole Derivatives: In vitro Cytotoxicity, Antimicrobial and Molecular Docking Studies

https://doi.org/10.14233/ajchem.2026.35287
Potharaju Sunil Kumar
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0009-0963-9461
Rambabu Bhukya
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0002-2343-0807
Chandulal Bhukya
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0006-2068-8940
Nampally Rajitha
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0009-7965-1220
Goli J. Rupasree
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0003-6032-0073
Nalaparaju Nagaraju
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0000-0001-7418-8390
Ramchander Jadhav
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0000-0003-3472-2581

Corresponding Author(s) : Ramchander Jadhav

ramorgchemou@gmail.com

Asian Journal of Chemistry, Vol. 38 No. 5 (2026): Vol 38, Issue 5, 2026

Abstract

A series of novel hydrazone-linked 1,2,3-triazole-pyrazole derivatives (7a-l) were rationally designed and synthesised through an efficient multistep synthetic strategy. The key intermediates were constructed via diazotisation–azidation followed by cycloaddition to generate the 1,2,3-triazole core, which was further functionalised to afford the target hydrazone derivatives. Final compounds were evaluated for their in vitro anticancer and antimicrobial activities. Antiproliferative screening against selected human cancer cell lines revealed that compounds bearing electron-withdrawing substituents exhibited superior cytotoxicity compared to electron-donating analogues. Among the synthesised derivatives, 7d (p-Cl) and 7c (p-NO2) exhibited the lowest IC50 values against the MCF-7 cell line (0.10 and 0.55 µM, respectively), comparable to doxorubicin (0.92 µM) under the same conditions. In antibacterial assays, halogen and fluoro-substituted derivatives demonstrated comparatively improved activity, with compounds 7b, 7d, 7i and 7k showing notable potency. Antifungal evaluation revealed that nitro-, fluoro- and methoxy-substituted analogues, particularly 7c, 7e and 7f, displayed enhanced activity against the tested strains. Molecular docking studies suggested favourable binding interactions with selected biological targets. Based on the obtained results, it is concluded that hydrazone-linked 1,2,3-triazole-pyrazole hybrids act as promising scaffolds for further optimisation toward anticancer and antimicrobial applications.

Keywords

Hydrazone derivatives 1,2,3-Triazole-pyrazole hybrids Cytotoxicity activity Antimicrobial activity Molecular docking
(1)
Kumar, P. S.; Bhukya, R.; Bhukya, C.; Rajitha, N.; Rupasree, G. J.; Nagaraju, N.; Jadhav, R. Design and Synthesis of Novel Hydrazone-Linked 1,2,3-Triazole-Pyrazole Derivatives: In Vitro Cytotoxicity, Antimicrobial and Molecular Docking Studies. ajc 2026, 38, 1324-1332.
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. D. Lengerli, K. Ibis, Y. Nural and E. Banoglu, Expert Opin. Drug Disc., 17, 1209 (2022); https://doi.org/10.1080/17460441.2022.2129613
  2. M.J. Vaishnani, S. Bijani, M. Rahamathulla, L. Baldaniya, V. Jain, K.Y. Thajudeen and I. Pasha, Green Chem. Lett. Rev., 17, 2307989 (2024); https://doi.org/10.1080/17518253.2024.2307989
  3. D. Veeranna, L. Ramdas, G. Ravi, S. Bujji, V. Thumma and J. Ramchander, ChemistrySelect, 7, e202201758 (2022); https://doi.org/10.1002/slct.202201758
  4. R. Bhukya, M.K. Vanga, V. Thumma, A. Mudiraj, N. Ranjan, P.B. Phanithi and R. Jadhav, J. Mol. Struct., 1349, 143865, (2026); https://doi.org/10.1016/j.molstruc.2025.143865
  5. A. Tan, J. Mol. Struct.. 1211, 128060 (2020); https://doi.org/10.1016/j.molstruc.2020.128060
  6. R. Gondru, S. Kanugala, S. Raj, C.G. Kumar, M. Pasupuleti, J. Banothu and R. Bavantula, Bioorg. Med. Chem. Lett., 33, 127746 (2021); https://doi.org/10.1016/j.bmcl.2020.127746
  7. T.B. de Souza, I.S. Caldas, F.S. Paula, C.C. Rodrigues, D.T. Carvalho, and D.F. Dias, Chem. Biol. Drug Des., 95, 124 (2020); https://doi.org/10.1111/cbdd.13628
  8. R. Bhukya, M.K. Vanga, C. Bhukya, V. Thumma and R. Jadhav, Chem. Biodiver., 22, 3184, (2025); https://doi.org/10.1002/cbdv.202403184
  9. M.C. Ríos and J. Portilla, Chemistry, 4, 940 (2022); https://doi.org/10.3390/chemistry4030065
  10. S. Mor, M. Khatri, R. Punia, S. Nagoria and S. Sindhu, Mini-Rev. Org. Chem., 19, 717 (2022); https://doi.org/10.2174/1570193X19666220118111614.
  11. E. Ameziane, I. Hassani, K. Rouzi, H. Assila, K. Karrouchi and M.H. Ansar, Reactions, 4, 478 (2023); https://doi.org/10.3390/reactions4030029
  12. A.A. Abu‐Hashem, J. Heterocycl. Chem., 58, 805 (2021); https://doi.org/10.1002/jhet.4216.
  13. R. Matta, J. Pochampally, B.N. Dhoddi, S. Bhookya, S. Bitla and A. Gayatri, BMC Chem., 17, 61 (2023); https://doi.org/10.1186/s13065-023-00965-8.
  14. M. Assali, M. Abualhasan, H. Sawaftah, M. Hawash and A. Mousa, J. Chem., 2020, 6393428 (2020); https://doi.org/10.1155/2020/6393428.
  15. S.M. Jagadale, Y.K. Abhale, H.R. Pawar, A. Shinde, V.D. Bobade, A.P. Chavan, D. Sarkar and P.C. Mhaske, Polycycl. Arom. Comp., 42, 3216 (2020); https://doi.org/10.1080/10406638.2020.1857272
  16. G.B.N.V.N. Kolukula, S. Subramanyam, T.R. Allaka and M.Z. Ahmed, Chem. Biodiver., 22, e202401810 (2025); https://doi.org/10.1002/cbdv.202401810
  17. K.B. Gangurde, R.A. More, V.A. Adole and D.S. Ghotekar, J. Mol. Struct., 1299, 136760 (2024); https://doi.org/10.1016/j.molstruc.2023.136760.
  18. C.B. de Oliveira, J. França, T.C. LaPlante and S.R. Villar, Mini-Rev. Org. Chem., 20, 342 (2020); https://doi.org/10.2174/1389557519666191014142448
  19. E.R. Belyaeva, Y.V. Myasoedova, N.M. Ishmuratova and G.Y. Ishmuratov, Russ. J. Bioorg. Chem., 48, 1123 (2022); https://doi.org/10.1134/S1068162022060085
  20. D. Tzankova, S. Vladimirova, D. Aluani, Y. Yordanov, L. Peikova and M. Georgieva, Acta Pharm., 70, 303 (2020); https://doi.org/10.2478/acph-2020-0026
  21. K.D. Katariya, S.R. Shah and D. Reddy, Bioorg. Chem., 94, 103406 (2020); https://doi.org/10.1016/j.bioorg.2019.103406
  22. S. Senthilkumar, J. Seralathan and G. Muthukumaran, J. Mol. Struct., 1226, 129354 (2021); https://doi.org/10.1016/j.molstruc.2020.129354.
  23. N. Fatima, A. Saeed, S. Ullah, S.A. Halim, A. Khan, M. Yaseen, M.Z. Hashmi, A. Mumtaz, H.R. El-Seedi, J. Uddin and A. Al-Harrasi, Bioorg. Chem., 153, 107822 (2024); https://doi.org/10.1016/j.bioorg.2024.107822
  24. M. Marzi, M. Farjam, Z. Kazeminejad, A. Shiroudi, A. Kouhpayeh and E. Zarenezhad, J. Chem., 2022, 7884316 (2022); https://doi.org/10.1155/2022/7884316
  25. B. Sharma, S. Kumar, J. Preeti, M.D. Johansen, L. Kremer and V. Kumar, Chem. Biol. Drug Des., 99, 301 (2022); https://doi.org/10.1111/cbdd.13984
  26. S. Rollas and Ş.G. Küçükgüzel, Molecules, 12, 1910 (2007); https://doi.org/10.3390/12081910
  27. G. Verma, A. Marella, M. Shaquiquzzaman, M. Akhtar, M. R. Ali and M.M. Alam, J. Pharm. Bioallied Sci., 6, 69 (2014); https://doi.org/10.4103/0975-7406.129170
  28. B. Koçyiğit-Kaymakçıoğlu, E. Oruç, S. Unsalan, F. Kandemirli, N. Shvets, S. Rollas and A. Dimoglo, Bioorg. Med. Chem. Lett., 41, 1253 (2006); https://doi.org/10.1016/j.ejmech.2006.06.009
  29. B. Koçyiğit-Kaymakçıoğlu, E. Oruç, S. Unsalan, F. Kandemirli, N. Shvets, S. Rollas and A. Dimoglo, Eur. J. Med. Chem., 38, 1005 (2003); https://doi.org/10.1016/j.ejmech.2003.08.004
  30. S.G. Agalave, S.R. Maujan and V.S. Pore, Chem. Asian J., 6, 2696 (2011); https://doi.org/10.1002/asia.201100432
  31. C.-H. Zhou and Y. Wang, Curr. Med. Chem., 19, 239 (2012); https://doi.org/10.2174/092986712803414213
  32. H.C. Kolb, M.G. Finn and K.B. Sharpless, Angew. Chem. Int. Ed., 40, 2004 (2001); https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO; 2-5
  33. J.E. Moses and A.D. Moorhouse, Chem. Soc. Rev., 36, 1249 (2007); https://doi.org/10.1039/B613014N
  34. B. S. Holla, B. Veerendra, M. K. Shivananda and B. Poojary, Eur. J. Med. Chem., 37, 511 (2002); https://doi.org/10.1016/S0223-5234(02)01358-2
  35. S. Fustero, M. Sánchez-Roselló, P. Barrio and A. Simon-Fuentes, Chem. Rev., 111, 6984 (2011); https://doi.org/10.1021/cr2000459
  36. A. Ansari, A. Ali and M. Asif, New J. Chem., 41, 16 (2017); https://doi.org/10.1039/C6NJ03181A
  37. J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, p. 283 (1976).
  38. A.A. Bekhit and T. Abdel-Aziem, Bioorg. Med. Chem., 12, 1935 (2004); https://doi.org/10.1016/j.bmc.2004.01.037
  39. S. Kumar, S. Bawa and H. Gupta, Mini Rev. Med. Chem., 9, 1648 (2009); https://doi.org/10.2174/138955709791012247
  40. K. Nepali, S. Sharma, M. Sharma, P.M.S. Bedi and K.L. Dhar, Eur. J. Med. Chem., 77, 422 (2014); https://doi.org/10.1016/j.ejmech.2014.03.018
  41. R. Morphy and Z. Rankovic, J. Med. Chem., 48, 6523 (2005); https://doi.org/10.1021/jm058225d
  42. C.-H. Yun, T. J. Boggon, Y. Li, M. S. Woo, H. Greulich, M. Meyerson and M.J. Eck, Cancer Cell, 11, 217 (2007); https://doi.org/10.1016/j.ccr.2006.12.017
Read More
Author biographies is not available.
Crossref
Scopus
Google Scholar
Europe PMC
Download
PDF
Statistic
Read Counter : 0 Download : 0
PlumX