Copyright (c) 2025 Quang Trung Nguyen, Phuong Nam Pham Thi

This work is licensed under a Creative Commons Attribution 4.0 International License.
Zinc(II) Complexes Containing Aromatic Hydrazones: Synthesis, Spectral Characterization, Luminescent Properties and a-Glucosidase Inhibition
Corresponding Author(s) : Quang Trung Nguyen
Asian Journal of Chemistry,
Vol. 37 No. 5 (2025): Vol 37 Issue 5, 2025
Abstract
Four zinc(II) complexes were synthesized by the coordinating Zn2+ ions with novel aromatic hydrazone ligands. Based on the spectral analyses, the molecular ratio of Zn(II) ions to hydrazone ligands was established as 1:2, and a tetrahedral geometry around the zinc metal center was proposed for the synthesized aromatic hydrazone zinc(II) complexes. The aromatic hydrazone ligands probably coordinated with the metal Zn2+ via the carbonyl oxygen and deprotonated oxygen of salicyl ring. The fluorescence spectra of the synthesized zinc(II) complexes were analyzed in dichloromethane, revealing that the aromatic hydrazone ligands with various substituents generated a blue shift in the maximum emissions of the corresponding zinc(II) complexes. The inhibition of α-glucosidase by the synthesized hydrazone compounds was evaluated, and based on the antidiabetic activity results, the synthesized zinc(II) complexes demonstrate superior efficacy compared to the corresponding aromatic hydrazone ligands.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- P.C. Sharma, D. Sharma, A. Sharma, N. Saini, R. Goyal, M. Ola, R. Chawla and V.K. Thakur, Mater. Today Chem., 18, 100349 (2020); https://doi.org/10.1016/j.mtchem.2020.100349
- A.-M. Stadler and J. Harrowûeld, Inorg. Chim. Acta, 362, 4298 (2009); https://doi.org/10.1016/j.ica.2009.05.062
- H. Kargar, M. Fallah-Mehrjardi and K.S. Munawar, Coord. Chem. Rev., 501, 215587 (2024); https://doi.org/10.1016/j.ccr.2023.215587
- O.M.I. Adly and A. Taha, J. Mol. Struct., 1038, 250 (2013); https://doi.org/10.1016/j.molstruc.2013.01.035
- P. Yang, H. Chen, Z.-Z. Wang, L.-L. Zhang, D.-D. Zhang, Q.-S. Shi and X.-B. Xie, J. Inorg. Biochem., 213, 111248 (2020); https://doi.org/10.1016/j.jinorgbio.2020.111248
- M.K. Hossain, M. Haukka, G.C. Lisensky, M.G. Richmond and E. Nordlander, Polyhedron, 258, 117020 (2024); https://doi.org/10.1016/j.poly.2024.117020
- M. Fallah-Mehrjardi, H. Kargar and K.S. Munawar, Inorg. Chim. Acta, 560, 121835 (2024); https://doi.org/10.1016/j.ica.2023.121835
- S.D. Kurbah, M. Asthana, I. Syiemlieh and R.A. Lal, Curr. Organocatal., 4, 189 (2018); https://doi.org/10.2174/2213337205666180124161832
- C. Shalini, M. Akilesh, G. Sathiyaraj, N.S.P. Bhuvanesh, K.S. Neethu, M.V. Kaveri and N. Dharmaraj, Appl. Organomet. Chem., 38, e7709 (2024); https://doi.org/10.1002/aoc.7709
- H.A. El-Ghamry, M. Gaber, F.M. Alkhatib, H.F. Al Shareef, K.M. Takroni and S.K. Fathalla, RSC Adv., 14, 30673 (2024); https://doi.org/10.1039/D4RA05769D
- A. Ciupa, RSC Adv., 15, 3465 (2025); https://doi.org/10.1039/D4RA09068C
- S.A. Rupa, A.M.P. Md, W.E. Ghann and A. Abdullahi, RSC Adv., 13, 23819 (2023); https://doi.org/10.1039/D3RA04364A
- Z.-H. Zhang, Y.-M. Zhang, X.-T. Kan, Q.-Y. Yang, Y.-J. Li, T.-B. Wei, H. Yao and Q. Lin, Dyes Pigments, 191, 109389 (2021); https://doi.org/10.1016/j.dyepig.2021.109389
- Y. Zhang, Q. Li, Q. Zhang, Q. Lin, C. Cao, M. Liu and T. Wei, Chin. J. Chem., 29, 1529 (2011); https://doi.org/10.1002/cjoc.201180275
- M. Saravanan and S. Abraham Rajasekar, Opt. Mater., 54, 217 (2016); https://doi.org/10.1016/j.optmat.2016.02.039
- T.A. Khattab, Mater. Chem. Phys., 254, 123456 (2020); https://doi.org/10.1016/j.matchemphys.2020.123456
- R.M. Snari, M. Alsahag, A. Alisaac, A. Bayazeed, A. Alsoliemy, M.E. Khalifa and N.M. El-Metwaly, J. Mol. Liq., 366, 120149 (2022); https://doi.org/10.1016/j.molliq.2022.120149
- P. Popczyk, A. Ghinet, C. Bortolus, L. Kamus, M.F. Lensink, J. de Ruyck, B. Sendid and F. Dubar, J. Enzyme Inhib. Med. Chem., 39, 2429109 (2024); https://doi.org/10.1080/14756366.2024.2429109
- M.S. Alam, S.-U. Choi and D.-U. Lee, Bioorg. Med. Chem., 25, 389 (2016); https://doi.org/10.1016/j.bmc.2016.11.005
- L. Popiolek, A. Biernasiuk, A. Berecka, A. Gumieniczek, A. Malm and M. Wujec, Chem. Biol. Drug Des., 91, 915 (2018); https://doi.org/10.1111/cbdd.13158
- S. Emami, M. Valipour, F.K. Komishani, F. Sadati-Ashrafi, M. Rasoulian, M. Ghasemian, M. Tajbakhsh, P.H. Masihi, A. Shakiba, H. Irannejad and N. Ahangar, Bioorg. Chem., 112, 104943 (2021); https://doi.org/10.1016/j.bioorg.2021.104943
- N. Agrawal, R. Mishra, S. Pathak, A. Goyal and K. Shah, Lett. Org. Chem., 20, 123 (2023); https://doi.org/10.2174/1570178619666220831122614
- B.R. Thorat, S.N. Mali, D. Rani and R.S. Yamgar, Curr. Computeraided Drug Des., 17, 294 (2021); https://doi.org/10.2174/1573409916666200302120942
- H. Ünver, B. Berber, R. Demirel and A.T. Koparal, Anticancer. Agents Med. Chem., 19, 1658 (2019); https://doi.org/10.2174/1871520619666190318125824
- M. Yousaf, M. Khan, M. Ali, W.A. Shams, M. Ali, Curr. Bioact. Compd., 18, e190422203781 (2022); https://doi.org/10.2174/1573407218666220419105140
- J. Zhao, Y. Wang, W. Chen, G. Hao, J. Sun, Q. Shi, F. Tian and R. Ma, RSC Adv., 12, 3073 (2022); https://doi.org/10.1039/D1RA08616B
- Z. Moussa, M. Al-Mamary, S. Al-Juhani and S.A. Ahmed, Heliyon, 6, e05019 (2020); https://doi.org/10.1016/j.heliyon.2020.e05019
- Ü.Ö. Özdemir, N. Akkaya and N. Özbek, Inorg. Chim. Acta, 400, 13 (2013); https://doi.org/10.1016/j.ica.2013.01.031
- T. Benkovic, A. Kendel, J. Parlov-Vukovic, D. Kontrec, V. Chis, S. Miljanic and N. Galic, Spectrochim. Acta A Mol. Biomol. Spectrosc., 190, 259 (2018); https://doi.org/10.1016/j.saa.2017.09.038
- X. Wang, S.-W. Yan, J. Yang, D.-R. Xiao, H.-Y. Zhang, J.-L. Zhang, X.-L. Chi and E.-B. Wang, Inorg. Chim. Acta, 409, 208 (2014); https://doi.org/10.1016/j.ica.2013.09.031
- L. Rochette, M. Zeller, Y. Cottin and C. Vergely, Biochim. Biophys. Acta, Gen. Subj., 1840, 2709 (2014); https://doi.org/10.1016/j.bbagen.2014.05.017
- F.M. Ashcroft and P. Rorsman, Cell, 148, 1160 (2012); https://doi.org/10.1016/j.cell.2012.02.010
- C.-H. Chang, Y.-D. Jiang, C.-H. Chung, L.-T. Ho and L.-M. Chuang, J. Formos. Med. Assoc., 111, 617 (2012); https://doi.org/10.1016/j.jfma.2012.09.009
- M. Dhameja and P. Gupta, Eur. J. Med. Chem., 176, 343 (2019); https://doi.org/10.1016/j.ejmech.2019.04.025
- U. Ghani, Eur. J. Med. Chem., 103, 133 (2015); https://doi.org/10.1016/j.ejmech.2015.08.043
- S. Malik, M.A. Lodhi, S. Ayaz and Z. Ullah, J. Mol. Liq., 400, 124572 (2024); https://doi.org/10.1016/j.molliq.2024.124572
- C.I. Chukwumaa, S.S. Mashelea, K.C. Ezeb, G.R. Matowanea and S. Md, Pharmacol. Res., 155, 104744 (2020); https://doi.org/10.1016/j.phrs.2020.104744
- M. Huseynovaa, A. Medjidov, P. Taslimi and M. Aliyeva, Bioorg. Chem., 83, 55 (2019); https://doi.org/10.1016/j.bioorg.2018.10.012
- Y. Yoshikawa and H. Yasui, Curr. Top. Med. Chem., 12, 210 (2012); https://doi.org/10.2174/156802612799078874
- G.M. Esteban-Parra, E. San Sebastián, J. Cepeda, C. Sánchez-González, L. Rivas-García, J. Llopis, P. Aranda, M. Sánchez-Moreno, M. Quirós and A. Rodríguez-Diéguez, J. Inorg. Biochem., 212, 111235 (2020); https://doi.org/10.1016/j.jinorgbio.2020.111235
- M. Demurtas, A. Baldisserotto, I. Lampronti, D. Moi, G. Balboni, S. Pacifico, S. Vertuani, S. Manfredini and V. Onnis, Bioorg. Chem., 85, 568 (2019); https://doi.org/10.1016/j.bioorg.2019.02.007
- C.B. Juliana de Oliveira, C.C.F. Tanos, S.R. LaPlante and D.F.V. José, Mini Rev. Med. Chem., 20, 342 (2020); https://doi.org/10.2174/1389557519666191014142448
- A.M. John, J. Jose, R. Thomas, K.J. Thomas and S.P. Balakrishnan, Spectrochim. Acta Part A: Mol. Biomol. Spect., 236, 118329 (2020); https://doi.org/10.1016/j.saa.2020.118329
- M.C. Mandewale, B. Thorat, Y. Nivid, R. Jadhav, A. Nagarsekar and R. Yamgar, J. Saudi Chem. Soc., 22, 218 (2018); https://doi.org/10.1016/j.jscs.2016.04.003
- B. Kumar, J. Devi, A. Dubey, A. Tufail and B. Taxak, Sci. Rep., 13, 15906 (2023); https://doi.org/10.1038/s41598-023-42180-4
- E.N. Agbo, Res. Chem., 14, 102102 (2025); https://doi.org/10.1016/j.rechem.2025.102102
- D. Avci, S. Altürk, F. Sönmez, Ö. Tamer, A. Basoglu, Y. Atalay, B.Z. Kurt and N. Dege, J. Mol. Struct., 1197, 645 (2019); https://doi.org/10.1016/j.molstruc.2019.07.039
- E. Pahontu, D.-C. Ilies, S. Shova, C. Oprean, V. Pãunescu, O.T. Olaru, F.S. Rãdulescu, A. Gulea, T. Rosu and D. Drãgãnescu, Molecules, 22, 650 (2017); https://doi.org/10.3390/molecules22040650
- M.C. Mandewale, B. Thorat, D. Shelke and R. Yamgar, Bioinorg. Chem. Appl., 2015, 153015 (2015); https://doi.org/10.1155/2015/153015
- M.C. Mandewale, S. Kokate, B. Thorat, S. Sawant and R. Yamgar, Arab. J. Chem., 12, 4479 (2016); https://doi.org/10.1016/j.arabjc.2016.07.016
- L. Li, Y.Z. Zhang, E. Liu, C. Yang, J.A. Golen, A.L. Rheingold and G. Zhang, J. Mol. Struct., 1110, 180 (2016); https://doi.org/10.1016/j.molstruc.2016.01.051
- S. Aslkhademi, N. Noshiranzadeh, M.S. Sadjadi, K. Mehrani and N. Farhadyar, Polyhedron, 160, 115 (2019); https://doi.org/10.1016/j.poly.2018.12.023
- M.C. Mandewale, S. Kokate, B. Thorat, S. Sawant and R. Yamgar, Arab. J. Chem., 12, 4479 (2019); https://doi.org/10.1016/j.arabjc.2016.07.016
- N. Sunitha, C.I.S. Raj and B.S. Kumari, Res. Chem., 4, 100588 (2022); https://doi.org/10.1016/j.rechem.2022.100588
References
P.C. Sharma, D. Sharma, A. Sharma, N. Saini, R. Goyal, M. Ola, R. Chawla and V.K. Thakur, Mater. Today Chem., 18, 100349 (2020); https://doi.org/10.1016/j.mtchem.2020.100349
A.-M. Stadler and J. Harrowûeld, Inorg. Chim. Acta, 362, 4298 (2009); https://doi.org/10.1016/j.ica.2009.05.062
H. Kargar, M. Fallah-Mehrjardi and K.S. Munawar, Coord. Chem. Rev., 501, 215587 (2024); https://doi.org/10.1016/j.ccr.2023.215587
O.M.I. Adly and A. Taha, J. Mol. Struct., 1038, 250 (2013); https://doi.org/10.1016/j.molstruc.2013.01.035
P. Yang, H. Chen, Z.-Z. Wang, L.-L. Zhang, D.-D. Zhang, Q.-S. Shi and X.-B. Xie, J. Inorg. Biochem., 213, 111248 (2020); https://doi.org/10.1016/j.jinorgbio.2020.111248
M.K. Hossain, M. Haukka, G.C. Lisensky, M.G. Richmond and E. Nordlander, Polyhedron, 258, 117020 (2024); https://doi.org/10.1016/j.poly.2024.117020
M. Fallah-Mehrjardi, H. Kargar and K.S. Munawar, Inorg. Chim. Acta, 560, 121835 (2024); https://doi.org/10.1016/j.ica.2023.121835
S.D. Kurbah, M. Asthana, I. Syiemlieh and R.A. Lal, Curr. Organocatal., 4, 189 (2018); https://doi.org/10.2174/2213337205666180124161832
C. Shalini, M. Akilesh, G. Sathiyaraj, N.S.P. Bhuvanesh, K.S. Neethu, M.V. Kaveri and N. Dharmaraj, Appl. Organomet. Chem., 38, e7709 (2024); https://doi.org/10.1002/aoc.7709
H.A. El-Ghamry, M. Gaber, F.M. Alkhatib, H.F. Al Shareef, K.M. Takroni and S.K. Fathalla, RSC Adv., 14, 30673 (2024); https://doi.org/10.1039/D4RA05769D
A. Ciupa, RSC Adv., 15, 3465 (2025); https://doi.org/10.1039/D4RA09068C
S.A. Rupa, A.M.P. Md, W.E. Ghann and A. Abdullahi, RSC Adv., 13, 23819 (2023); https://doi.org/10.1039/D3RA04364A
Z.-H. Zhang, Y.-M. Zhang, X.-T. Kan, Q.-Y. Yang, Y.-J. Li, T.-B. Wei, H. Yao and Q. Lin, Dyes Pigments, 191, 109389 (2021); https://doi.org/10.1016/j.dyepig.2021.109389
Y. Zhang, Q. Li, Q. Zhang, Q. Lin, C. Cao, M. Liu and T. Wei, Chin. J. Chem., 29, 1529 (2011); https://doi.org/10.1002/cjoc.201180275
M. Saravanan and S. Abraham Rajasekar, Opt. Mater., 54, 217 (2016); https://doi.org/10.1016/j.optmat.2016.02.039
T.A. Khattab, Mater. Chem. Phys., 254, 123456 (2020); https://doi.org/10.1016/j.matchemphys.2020.123456
R.M. Snari, M. Alsahag, A. Alisaac, A. Bayazeed, A. Alsoliemy, M.E. Khalifa and N.M. El-Metwaly, J. Mol. Liq., 366, 120149 (2022); https://doi.org/10.1016/j.molliq.2022.120149
P. Popczyk, A. Ghinet, C. Bortolus, L. Kamus, M.F. Lensink, J. de Ruyck, B. Sendid and F. Dubar, J. Enzyme Inhib. Med. Chem., 39, 2429109 (2024); https://doi.org/10.1080/14756366.2024.2429109
M.S. Alam, S.-U. Choi and D.-U. Lee, Bioorg. Med. Chem., 25, 389 (2016); https://doi.org/10.1016/j.bmc.2016.11.005
L. Popiolek, A. Biernasiuk, A. Berecka, A. Gumieniczek, A. Malm and M. Wujec, Chem. Biol. Drug Des., 91, 915 (2018); https://doi.org/10.1111/cbdd.13158
S. Emami, M. Valipour, F.K. Komishani, F. Sadati-Ashrafi, M. Rasoulian, M. Ghasemian, M. Tajbakhsh, P.H. Masihi, A. Shakiba, H. Irannejad and N. Ahangar, Bioorg. Chem., 112, 104943 (2021); https://doi.org/10.1016/j.bioorg.2021.104943
N. Agrawal, R. Mishra, S. Pathak, A. Goyal and K. Shah, Lett. Org. Chem., 20, 123 (2023); https://doi.org/10.2174/1570178619666220831122614
B.R. Thorat, S.N. Mali, D. Rani and R.S. Yamgar, Curr. Computeraided Drug Des., 17, 294 (2021); https://doi.org/10.2174/1573409916666200302120942
H. Ünver, B. Berber, R. Demirel and A.T. Koparal, Anticancer. Agents Med. Chem., 19, 1658 (2019); https://doi.org/10.2174/1871520619666190318125824
M. Yousaf, M. Khan, M. Ali, W.A. Shams, M. Ali, Curr. Bioact. Compd., 18, e190422203781 (2022); https://doi.org/10.2174/1573407218666220419105140
J. Zhao, Y. Wang, W. Chen, G. Hao, J. Sun, Q. Shi, F. Tian and R. Ma, RSC Adv., 12, 3073 (2022); https://doi.org/10.1039/D1RA08616B
Z. Moussa, M. Al-Mamary, S. Al-Juhani and S.A. Ahmed, Heliyon, 6, e05019 (2020); https://doi.org/10.1016/j.heliyon.2020.e05019
Ü.Ö. Özdemir, N. Akkaya and N. Özbek, Inorg. Chim. Acta, 400, 13 (2013); https://doi.org/10.1016/j.ica.2013.01.031
T. Benkovic, A. Kendel, J. Parlov-Vukovic, D. Kontrec, V. Chis, S. Miljanic and N. Galic, Spectrochim. Acta A Mol. Biomol. Spectrosc., 190, 259 (2018); https://doi.org/10.1016/j.saa.2017.09.038
X. Wang, S.-W. Yan, J. Yang, D.-R. Xiao, H.-Y. Zhang, J.-L. Zhang, X.-L. Chi and E.-B. Wang, Inorg. Chim. Acta, 409, 208 (2014); https://doi.org/10.1016/j.ica.2013.09.031
L. Rochette, M. Zeller, Y. Cottin and C. Vergely, Biochim. Biophys. Acta, Gen. Subj., 1840, 2709 (2014); https://doi.org/10.1016/j.bbagen.2014.05.017
F.M. Ashcroft and P. Rorsman, Cell, 148, 1160 (2012); https://doi.org/10.1016/j.cell.2012.02.010
C.-H. Chang, Y.-D. Jiang, C.-H. Chung, L.-T. Ho and L.-M. Chuang, J. Formos. Med. Assoc., 111, 617 (2012); https://doi.org/10.1016/j.jfma.2012.09.009
M. Dhameja and P. Gupta, Eur. J. Med. Chem., 176, 343 (2019); https://doi.org/10.1016/j.ejmech.2019.04.025
U. Ghani, Eur. J. Med. Chem., 103, 133 (2015); https://doi.org/10.1016/j.ejmech.2015.08.043
S. Malik, M.A. Lodhi, S. Ayaz and Z. Ullah, J. Mol. Liq., 400, 124572 (2024); https://doi.org/10.1016/j.molliq.2024.124572
C.I. Chukwumaa, S.S. Mashelea, K.C. Ezeb, G.R. Matowanea and S. Md, Pharmacol. Res., 155, 104744 (2020); https://doi.org/10.1016/j.phrs.2020.104744
M. Huseynovaa, A. Medjidov, P. Taslimi and M. Aliyeva, Bioorg. Chem., 83, 55 (2019); https://doi.org/10.1016/j.bioorg.2018.10.012
Y. Yoshikawa and H. Yasui, Curr. Top. Med. Chem., 12, 210 (2012); https://doi.org/10.2174/156802612799078874
G.M. Esteban-Parra, E. San Sebastián, J. Cepeda, C. Sánchez-González, L. Rivas-García, J. Llopis, P. Aranda, M. Sánchez-Moreno, M. Quirós and A. Rodríguez-Diéguez, J. Inorg. Biochem., 212, 111235 (2020); https://doi.org/10.1016/j.jinorgbio.2020.111235
M. Demurtas, A. Baldisserotto, I. Lampronti, D. Moi, G. Balboni, S. Pacifico, S. Vertuani, S. Manfredini and V. Onnis, Bioorg. Chem., 85, 568 (2019); https://doi.org/10.1016/j.bioorg.2019.02.007
C.B. Juliana de Oliveira, C.C.F. Tanos, S.R. LaPlante and D.F.V. José, Mini Rev. Med. Chem., 20, 342 (2020); https://doi.org/10.2174/1389557519666191014142448
A.M. John, J. Jose, R. Thomas, K.J. Thomas and S.P. Balakrishnan, Spectrochim. Acta Part A: Mol. Biomol. Spect., 236, 118329 (2020); https://doi.org/10.1016/j.saa.2020.118329
M.C. Mandewale, B. Thorat, Y. Nivid, R. Jadhav, A. Nagarsekar and R. Yamgar, J. Saudi Chem. Soc., 22, 218 (2018); https://doi.org/10.1016/j.jscs.2016.04.003
B. Kumar, J. Devi, A. Dubey, A. Tufail and B. Taxak, Sci. Rep., 13, 15906 (2023); https://doi.org/10.1038/s41598-023-42180-4
E.N. Agbo, Res. Chem., 14, 102102 (2025); https://doi.org/10.1016/j.rechem.2025.102102
D. Avci, S. Altürk, F. Sönmez, Ö. Tamer, A. Basoglu, Y. Atalay, B.Z. Kurt and N. Dege, J. Mol. Struct., 1197, 645 (2019); https://doi.org/10.1016/j.molstruc.2019.07.039
E. Pahontu, D.-C. Ilies, S. Shova, C. Oprean, V. Pãunescu, O.T. Olaru, F.S. Rãdulescu, A. Gulea, T. Rosu and D. Drãgãnescu, Molecules, 22, 650 (2017); https://doi.org/10.3390/molecules22040650
M.C. Mandewale, B. Thorat, D. Shelke and R. Yamgar, Bioinorg. Chem. Appl., 2015, 153015 (2015); https://doi.org/10.1155/2015/153015
M.C. Mandewale, S. Kokate, B. Thorat, S. Sawant and R. Yamgar, Arab. J. Chem., 12, 4479 (2016); https://doi.org/10.1016/j.arabjc.2016.07.016
L. Li, Y.Z. Zhang, E. Liu, C. Yang, J.A. Golen, A.L. Rheingold and G. Zhang, J. Mol. Struct., 1110, 180 (2016); https://doi.org/10.1016/j.molstruc.2016.01.051
S. Aslkhademi, N. Noshiranzadeh, M.S. Sadjadi, K. Mehrani and N. Farhadyar, Polyhedron, 160, 115 (2019); https://doi.org/10.1016/j.poly.2018.12.023
M.C. Mandewale, S. Kokate, B. Thorat, S. Sawant and R. Yamgar, Arab. J. Chem., 12, 4479 (2019); https://doi.org/10.1016/j.arabjc.2016.07.016
N. Sunitha, C.I.S. Raj and B.S. Kumari, Res. Chem., 4, 100588 (2022); https://doi.org/10.1016/j.rechem.2022.100588