Copyright (c) 2025 Bhagyashree Salunkhe, Ratnamala Bendre, sharda Gadale

This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, in vitro Antimicrobial and Antiproliferative Potentials of Novel Carvacrol Based Schiff Base Derivatives
Corresponding Author(s) : Sharda Gadale
Asian Journal of Chemistry,
Vol. 37 No. 7 (2025): Vol 37 Issue 7, 2025
Abstract
A series of novel carvacrol based Schiff base derivatives (5-Cl, Nap, 3,5-Dibr, DEAS and 5-Br) were synthesized and characterized through FT-IR, 1H NMR and 13C NMR spectroscopic methods. The FT-IR confirmed the characteristic peak of imine (–CH=N–) at 1619-1514 cm-1, while the NMR spectra confirmed the arrangement of aromatic and aliphatic protons and carbons with halogen substitutions. The synthesized Schiff Base derivatives had significant biological activity, particularly Nap, 5-Br, and 3,5-Dibr, which exhibited high cytotoxicity against the A-549 lung cancer cell line. Antimicrobial assay indicated a strong lethality in brine shrimp assays and acceptable antibacterial activity, especially for 5-Cl and 3,5-Dibr, with minimum inhibitory concentrations (MIC). These findings confirm the structural integrity and pharmacological significance of Schiff bases, highlighting their usefulness in the development of anticancer and antibacterial drugs.
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- W. Maczka, M. Twardawska, M. Grabarczyk and K. Winska, Antibiotics, 12, 824 (2023); https://doi.org/10.3390/antibiotics12050824 DOI: https://doi.org/10.3390/antibiotics12050824
- S. Maisanaba, M. Llana-Ruiz-Cabello, D. Gutiérrez-Praena, S. Pichardo, M. Puerto, A.I. Prieto, A. Jos and A.M. Cameán, Food Rev. Int., 33, 447 (2017); https://doi.org/10.1080/87559129.2016.1175010 DOI: https://doi.org/10.1080/87559129.2016.1175010
- N.B. Rathod, P. Kulawik, F. Ozogul, J.M. Regenstein and Y. Ozogul, Trends Food Sci. Technol., 116, 733 (2021); https://doi.org/10.1016/j.tifs.2021.08.023 DOI: https://doi.org/10.1016/j.tifs.2021.08.023
- C.J. Dias, H.A. Costa, C.A. Alves Dias-Filho, A.C. Ferreira, B. Rodrigues, M.C. Irigoyen, A.C. Romão Borges, V. de Andadre Martins, F.C. Branco Vidal, R.M. Ribeiro, N.S. Filho and C.T. Mostarda, Eur. J. Pharmacol., 917, 174717 (2022); https://doi.org/10.1016/j.ejphar.2021.174717 DOI: https://doi.org/10.1016/j.ejphar.2021.174717
- G. Bayramoglu, H. Senturk, A. Bayramoglu, M. Uyanoglu, S. Colak, A. Ozmen and D. Kolankaya, Cytotechnology, 66, 251 (2014); https://doi.org/10.1007/s10616-013-9563-5 DOI: https://doi.org/10.1007/s10616-013-9563-5
- G. Chinigò, A. Fiorio Pla and D. Gkika, Front. Pharmacol., 11, 581455 (2020); https://doi.org/10.3389/fphar.2020.581455 DOI: https://doi.org/10.3389/fphar.2020.581455
- U.B. More, H.P. Narkhede, D.S. Dalal and P.P. Mahulikar, Synth. Commun., 37, 1957 (2007); https://doi.org/10.1080/00397910701354608 DOI: https://doi.org/10.1080/00397910701354608
- J. Mastelic, I. Jerkovic, I. Blaževic, M. Poljak-Blaži, S. Borovic, I. Ivancic-Bace, V. Smreèki, N. Žarkovic, K. Brèic-Kostic, D. Vikic-Topic and N. Müller, J. Agric. Food Chem., 56, 3989 (2008); https://doi.org/10.1021/jf073272v DOI: https://doi.org/10.1021/jf073272v
- M.I. Konaklieva, SLAS Discov.: Adv. Sci. Drug Discov., 24, 419 (2018); https://doi.org/10.1177/2472555218812657 DOI: https://doi.org/10.1177/2472555218812657
- E. Raczuk, B. Dmochowska, J. Samaszko-Fiertek and J. Madaj, Molecules, 27, 787 (2022); 10.3390/molecules27030787 DOI: https://doi.org/10.3390/molecules27030787
- A. Soroceanu and A. Bargan, Crystals, 12, 1436 (2022); https://doi.org/10.3390/cryst12101436 DOI: https://doi.org/10.3390/cryst12101436
- Z. Zhang, Q. Song, Y. Jin, Y. Feng, J. Li and K. Zhang, Metals, 13, 386 (2023); https://doi.org/10.3390/met13020386 DOI: https://doi.org/10.3390/met13020386
- C. Boulechfar, H. Ferkous, A. Delimi, A. Djedouani, A. Kahlouche, A. Boublia, A.S. Darwish, T. Lemaoui, R. Verma and Y. Benguerba, Inorg. Chem. Commun., 150, 110451 (2023); https://doi.org/10.1016/j.inoche.2023.110451 DOI: https://doi.org/10.1016/j.inoche.2023.110451
- Nidhi, Siddharam, D.P. Rao, A.K. Gautam, A. Verma and Y. Gautam, Results Chem., 13, 101941 (2025); https://doi.org/10.1016/j.rechem.2024.101941 DOI: https://doi.org/10.1016/j.rechem.2024.101941
- I. Mushtaq, M. Ahmad, M. Saleem and A. Ahmed, Futur. J. Pharm. Sci., 10, 16 (2024); https://doi.org/10.1186/s43094-024-00594-5 DOI: https://doi.org/10.1186/s43094-024-00594-5
- S. Thakur, A. Jaryal and A. Bhalla, Results Chem., 7, 101350 (2024); https://doi.org/10.1016/j.rechem.2024.101350 DOI: https://doi.org/10.1016/j.rechem.2024.101350
- Beena, D. Kumar and D.S. Rawat, Bioorg. Med. Chem. Lett., 23, 641 (2013); https://doi.org/10.1016/j.bmcl.2012.12.001 DOI: https://doi.org/10.1016/j.bmcl.2012.12.001
- B.N. Meyer, N.R. Ferrigni, J.E. Putnam, L.B. Jacobsen, D.E. Nichols and J.L. McLaughlin, Planta Med., 45, 31 (1982); https://doi.org/10.1055/s-2007-971236 DOI: https://doi.org/10.1055/s-2007-971236
- F. Baquero, J. Antimicrob. Chemother., 39(Suppl. A), 1 (1997); https://doi.org/10.1093/jac/39.suppl_1.1 DOI: https://doi.org/10.1093/jac/39.suppl_1.1
References
W. Maczka, M. Twardawska, M. Grabarczyk and K. Winska, Antibiotics, 12, 824 (2023); https://doi.org/10.3390/antibiotics12050824 DOI: https://doi.org/10.3390/antibiotics12050824
S. Maisanaba, M. Llana-Ruiz-Cabello, D. Gutiérrez-Praena, S. Pichardo, M. Puerto, A.I. Prieto, A. Jos and A.M. Cameán, Food Rev. Int., 33, 447 (2017); https://doi.org/10.1080/87559129.2016.1175010 DOI: https://doi.org/10.1080/87559129.2016.1175010
N.B. Rathod, P. Kulawik, F. Ozogul, J.M. Regenstein and Y. Ozogul, Trends Food Sci. Technol., 116, 733 (2021); https://doi.org/10.1016/j.tifs.2021.08.023 DOI: https://doi.org/10.1016/j.tifs.2021.08.023
C.J. Dias, H.A. Costa, C.A. Alves Dias-Filho, A.C. Ferreira, B. Rodrigues, M.C. Irigoyen, A.C. Romão Borges, V. de Andadre Martins, F.C. Branco Vidal, R.M. Ribeiro, N.S. Filho and C.T. Mostarda, Eur. J. Pharmacol., 917, 174717 (2022); https://doi.org/10.1016/j.ejphar.2021.174717 DOI: https://doi.org/10.1016/j.ejphar.2021.174717
G. Bayramoglu, H. Senturk, A. Bayramoglu, M. Uyanoglu, S. Colak, A. Ozmen and D. Kolankaya, Cytotechnology, 66, 251 (2014); https://doi.org/10.1007/s10616-013-9563-5 DOI: https://doi.org/10.1007/s10616-013-9563-5
G. Chinigò, A. Fiorio Pla and D. Gkika, Front. Pharmacol., 11, 581455 (2020); https://doi.org/10.3389/fphar.2020.581455 DOI: https://doi.org/10.3389/fphar.2020.581455
U.B. More, H.P. Narkhede, D.S. Dalal and P.P. Mahulikar, Synth. Commun., 37, 1957 (2007); https://doi.org/10.1080/00397910701354608 DOI: https://doi.org/10.1080/00397910701354608
J. Mastelic, I. Jerkovic, I. Blaževic, M. Poljak-Blaži, S. Borovic, I. Ivancic-Bace, V. Smreèki, N. Žarkovic, K. Brèic-Kostic, D. Vikic-Topic and N. Müller, J. Agric. Food Chem., 56, 3989 (2008); https://doi.org/10.1021/jf073272v DOI: https://doi.org/10.1021/jf073272v
M.I. Konaklieva, SLAS Discov.: Adv. Sci. Drug Discov., 24, 419 (2018); https://doi.org/10.1177/2472555218812657 DOI: https://doi.org/10.1177/2472555218812657
E. Raczuk, B. Dmochowska, J. Samaszko-Fiertek and J. Madaj, Molecules, 27, 787 (2022); 10.3390/molecules27030787 DOI: https://doi.org/10.3390/molecules27030787
A. Soroceanu and A. Bargan, Crystals, 12, 1436 (2022); https://doi.org/10.3390/cryst12101436 DOI: https://doi.org/10.3390/cryst12101436
Z. Zhang, Q. Song, Y. Jin, Y. Feng, J. Li and K. Zhang, Metals, 13, 386 (2023); https://doi.org/10.3390/met13020386 DOI: https://doi.org/10.3390/met13020386
C. Boulechfar, H. Ferkous, A. Delimi, A. Djedouani, A. Kahlouche, A. Boublia, A.S. Darwish, T. Lemaoui, R. Verma and Y. Benguerba, Inorg. Chem. Commun., 150, 110451 (2023); https://doi.org/10.1016/j.inoche.2023.110451 DOI: https://doi.org/10.1016/j.inoche.2023.110451
Nidhi, Siddharam, D.P. Rao, A.K. Gautam, A. Verma and Y. Gautam, Results Chem., 13, 101941 (2025); https://doi.org/10.1016/j.rechem.2024.101941 DOI: https://doi.org/10.1016/j.rechem.2024.101941
I. Mushtaq, M. Ahmad, M. Saleem and A. Ahmed, Futur. J. Pharm. Sci., 10, 16 (2024); https://doi.org/10.1186/s43094-024-00594-5 DOI: https://doi.org/10.1186/s43094-024-00594-5
S. Thakur, A. Jaryal and A. Bhalla, Results Chem., 7, 101350 (2024); https://doi.org/10.1016/j.rechem.2024.101350 DOI: https://doi.org/10.1016/j.rechem.2024.101350
Beena, D. Kumar and D.S. Rawat, Bioorg. Med. Chem. Lett., 23, 641 (2013); https://doi.org/10.1016/j.bmcl.2012.12.001 DOI: https://doi.org/10.1016/j.bmcl.2012.12.001
B.N. Meyer, N.R. Ferrigni, J.E. Putnam, L.B. Jacobsen, D.E. Nichols and J.L. McLaughlin, Planta Med., 45, 31 (1982); https://doi.org/10.1055/s-2007-971236 DOI: https://doi.org/10.1055/s-2007-971236
F. Baquero, J. Antimicrob. Chemother., 39(Suppl. A), 1 (1997); https://doi.org/10.1093/jac/39.suppl_1.1 DOI: https://doi.org/10.1093/jac/39.suppl_1.1