Abstract
In order to resist the growth of human pathogenic microorganisms, a new N-heterocyclic ligand of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-4-oxopiperidine-1-carbohydrazide was synthesised from the condensation reaction of 4-oxopiperidine-1-carbohydrazide and 2-hydroxynaphthalene-1-carbaldehyde in ethanol. Reaction of metal salt of (M(II/III)·Cl2)·nH2O M = Cr(III), Fe(III), Mn(II), Co(II), Ni(II) and Cu(II) with ligand resulted in the formation the two types of complexes [M(III)C17H19N3O5Cl] and [M(II)C17H20N3O5Cl] which adopted octahedral geometry. The ligand was thoroughly characterized by elemental analysis, FT-IR, UV–Vis, NMR (1H, 13C) and HR-mass spectroscopy while the structure of metal complexes was confirmed on the basis of elemental analysis, UV–Vis spectra, molar conductivity, magnetic susceptibility, and TGA-DTA analysis. The ligand behaves as dibasic tridentate, linkages via phenolic-O, azomethine-N, enolic-O atoms in metal (III) complexes and as monobasic tridentate in metal (II) complexes. The decomposition pattern were ascertained by TG analysis, and kinetics accountability from Coats–Redfern relation. The compounds were excited at λex = 380 nm and observed intense emission intensity at λem = λ527–533 nm. SEM analysis was performed to observe their surface analysis. The molecular geometry optimization and quantum chemical properties have been retrieved from DFT. ADMET score have been predicted as a drug-likeness prospect from admetSAR. The molecular docking outcomes revealed the good binding score of ligand with Adenylate kinase, Peptide deformylase (bacterial enzymes) and DNA polymerase (fungal enzyme). The in vitro antimicrobial potency of ligand and its metal complexes were carried against the bacterial species (Escherichia coli, Salmonella typhi, Staphylococcus aureus, Bacillus substilis), and fungal species (Candida albicans, Aspergillus niger) and showed their promising activity.
Graphical abstract
Similar content being viewed by others
Availability of data and materials
All the spectral data are provided supplementary information.
References
S. Kumar, J. Devi, A. Dubey, D. Kumar, D.K. Jindal, S. Asija, A. Sharma, Res. Chem. Intermed. 49, 939 (2023)
A. Erdmann, Y. Menon, C. Gros, V. Masson, Y. Aussagues, F. Ausseil, N. Novosad, P. Schambel, M. Baltas, P.B. Arimondo, Future Med. Chem. 8, 373 (2016)
W. Khalid, A. Badshah, A. UllahKhan, H. Nadeem, S. Ahmed, Chem. Cent. J. 12, 1 (2018)
U. Salgin-Goksen, G. Telli, A. Erikci, E. Dedecengiz, B.C. Tel, F.B. Kaynak, K. Yelekci, G. Ucar, N. Gokhan-Kelekci, J. Med. Chem. 64, 1989 (2021)
M. Gaber, A.M. Khedr, M. Elsharkawy, Appl. Organomet. Chem. 31, 1 (2017)
A. Alka, S. Gautam, R. Kumar, P. Singh, N. Gandhi, P. Jain, Results Chem. 5, 100849 (2023)
T.R.F. de Melo, R.C. Chelucci, M.E.L. Pires, L.A. Dutra, K.P. Barbieri, P.L. Bosquesi, G.H.G. Trossini, M.C. Chung, J.L. dos Santos, Int. J. Mol. Sci. 15, 5821 (2014)
W.B. Júnior, M.S. Alexandre-Moreira, M.A. Alves, A. Perez-Rebolledo, G.L. Parrilha, E.E. Castellano, O.E. Piro, E.J. Barreiro, L.M. Lima, H. Beraldo, Molecules 16, 6902 (2011)
X. Yu, L. Shi, S. Ke, Bioorg. Med. Chem. Lett. 25, 5772 (2015)
O.A. El-Gammal, G.M.A. El-Reash, R.A. Bedier, Appl. Organomet. Chem. 33, 1 (2019)
A.A. Mohamed, F.M. Ahmed, W.A. Zordok, W.H. El-Shwiniy, S.A. Sadeek, H.S. Elshafie, Inorganics 10, 1 (2022)
M.S. El-Attar, F.M. Ahmed, S.A. Sadeek, S.F. Mohamed, W.A. Zordok, W.H. El-Shwiniy, Appl. Organomet. Chem. 36, 10 (2022)
H.S. Seleem, G.A. El-Inany, B.A. El-Shetary, M.A. Mousa, F.I. Hanafy, Chem. Cent. J. 5, 1 (2011)
H.H. Repich, S.I. Orysyk, V.V. Orysyk, Y.L. Zborovskii, A.K. Melnyk, V.V. Trachevskyi, V.I. Pekhnyo, M.V. Vovk, J. Mol. Struct. 1146, 222 (2017)
J. Bureš, H. Jansová, J. Stariat, T. Filipský, P. Mladěnka, T. Šimůnek, R. Kučera, J. Klimeš, Q. Wang, K.J. Franz, P. Kovaříková, J. Pharma Biomed. Anal. 105, 55 (2015)
K.D. Praliev, N.A. Belikova, Zh.I. Isin, D.V. Sokolov, Pharm. Chem. J. 21, 854 (1987)
S.N. Mali, B.R. Thorat, D.R. Gupta, A. Pandey, MDPI Engn. Proc. 11, 1 (2021)
H.S. Seleem, Chem. Cent. J. 5, 1 (2011)
W. Cao, Y. Liu, T. Zhang, J. Jia, Polyhedron 147, 62 (2018)
R. Fouad, I.A. Shaaban, T.E. Ali, M.A. Assiri, S.S. Shenouda, RSC Adv. 11, 37726 (2021)
M. Gaber, S.K. Fathalla, H.A. El-Ghamry, Appl. Organo. Chem. 33, 1 (2019)
P. Jyothi, S. Koppu, V. Sumalatha, B. Ushaiah, C. Gyana Kumari, Inorg. Chem. Commun. 110, 107590 (2019)
M. Gaber, N. El-Wakiel, O.M. Hemeda, J. Mol. Struct. 1180, 318 (2019)
Y. Li, C. Qian, Y. Li, Y. Yang, D. Lin, X. Liu, C. Chen, J. Inorg. Biochem. 218, 111405 (2021)
F.K. Ommenya, E.A. Nyawade, D.M. Andala, J. Kinyua, J. Chem. 2020, ID1745236 (2020).
V.P. Singh, A. Katiyar, J. Coord. Chem. 61, 3200 (2008)
A. Pahonţu, C. Paraschivescu, D.C. Ilieş, D. Poirier, C. Oprean, V.P. Ǎunescu, A. Gulea, T. Roşu, O. Bratu, Molecules 21, 1 (2016)
L. Tabrizi, D.Q. Dao, T.A. Vu, RSC Adv. 9, 3320 (2019)
V.P. Singh, A. Katiyar, S. Singh, Biometals 21, 491 (2008)
G.M. Dongare, A.S. Aswar, Euro. J. Chem. 13, 4 (2022)
M. Shakir, S. Hanif, M.A. Sherwani, O. Mohammad, S.I. Al-Resayes, J. Mol. Struct. 1092, 143 (2015)
A.S. Alturiqi, A.N.M.A. Alaghaz, R.A. Ammar, M.E. Zayed, J. Chem. 2018, 8987 (2018)
A.K. Sarangi, B.B. Mahapatra, R.K. Mohapatra, S.K. Sethy, D. Das, L. Pintilie, M. Kudrat-E-Zahan, M. Azam, H. Meher, App. Organomet. Chem. 34, 1 (2020)
O.V. Konnik, M.A. Kiskin, D.S. Balaev, V.F. Shulgin, A.N. Gusev, J. Struct. Chem. 64, 1361–1368 (2023)
L.V. Ababei, A. Kriza, A.M. Musuc, C. Andronescu, E.A. Rogozea, J. Therm. Anal. Calorim. 101, 987 (2010)
S. Shit, J. Chakraborty, B. Samanta, A.M.Z. Slawin, V. Gramlich, S. Mitra, Struct. Chem. 20, 633 (2009)
O.M.I. Adly, Spectrochem. Acta Part A Mol. Biomol. Spectrosc. 79, 1295 (2011)
D. Meng, F. Liu, Y. Li, Z. Yang, G. Li, D. Guo, Luminescence 31, 507 (2016)
Y. Li, Z.Y. Yang, M.F. Wang, J. Fluorine 20, 891 (2010)
N. De Acha, C. Elosúa, J.M. Corres, F.J. Arregui, Sensors 19, 599 (2019)
R. Konakanchi, J. Haribabu, J. Prashanth, V.B. Nishtala, R. Mallela, S. Manchala, D. Gandamalla, R. Karvembu, B.V. Reddy, N.R. Yellu, L.R. Kotha, Appl. Organomet. Chem. 32, 1 (2018)
G. Tamasi, L. Chiasserini, L. Savini, A. Sega, R. Cini, J. Inorg. Biochem. 99, 1347 (2005)
K. Karrouchi, S. Fettach, A. El Hassane, I. Bayach, H. Albalwi, S. Arshad, N.K. Sebbar, H. Tachalait, K. Bougrin, F. My El Abbes, B. Himmi, Polycycl. Arom. Compd. 43, 2 (2023)
M. Bashir, A. A. Dar, and I. Yousuf, ACS Omega 8, (2023).
G.M. Dongare, A.S. Aswar, J. Saudi Chem. Soc. 25, 101325 (2021)
L.R. Domingo, M. Ríos-Gutiérrez, P. Pérez, Molecules 21, 748 (2016)
T.L. Yusuf, S.D. Oladipo, S. Zamisa, H.M. Kumalo, I.A. Lawal, M.M. Lawal, N. Mabuba, ACS Omega 6, 145 (2021)
R.G. Parr, C. Hill, N. Carolina, J. Am. Chem. Soc. 121, 1922 (1999)
G. Badhin, N.V. Likhanova, M.A. Domınguez-Aguilar, R. Martınez-Palou, V. Alberto, J.L. Gazquez, J. Phys. Chem. B 110, 8928 (2006)
F. Soleymani-Bonoti, M.A. Kamyabi, N. Arshadi, Comput. Theor. Chem. 1092, 47 (2016)
J.C. Guo, H.G. Lu, S.D. Li, Comput. Theor. Chem. 1018, 95 (2013)
A. Tabbiche, A. Bouchama, N. Chafai, F. Zaidi, C. Chiter, M. Yahiaoui, A. Abiza, J. Mol. Struct. 1261, 132865 (2022)
N.M. El-Barasi, M.M. Miloud, M.M. El-ajaily, R.K. Mohapatra, A.K. Sarangi, D. Das, A. Mahal, P.K. Parhi, L. Pintilie, S.R. Barik, M.N. AminBitu, M. Kudrat-E-Zahan, Z. Tabassum, S.I. Al-Resayes, M. Azam, J. Saudi Chem. Soc. 24, 492 (2020)
M. Sarkar, A. Nath, A. Kumer, C. Mallik, F. Akter, M. Moniruzzaman, M. Ali, J. Mol. Struct. 1244, 130953 (2021)
F. Cheng, W. Li, Y. Zhou, J. Shen, Z. Wu, G. Liu, P.W. Lee, Y. Tang, J. Chem. Inform. Mod. 52, 3099 (2012)
T. Khan, S. Dixit, R. Ahmad, S. Raza, I. Azad, S. Joshi, A.R. Khan, J. Chem. Bio. 10, 91 (2017)
C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 64, 4 (2012)
M. Aarjane, A. Aouidate, S. Slassi, A. Amine, Arab. J. Chem. 13, 6236 (2020)
A.C. Ekennia, E.C. Ibezim, O.C. Okpareke, C.U. Ibeji, C.J.O. Anarado, I. Babahan, B. Coban, B. Abulhasanov, F. Cömert, O.T. Ujam, Appl. Organ. Chem. 33, 1 (2019)
A. Misra, S. Sharma, D. Sharma, S. Dubey, A. Mishra, D. Kishore, J. Dwivedi, J. Chem. Sci. 130, 31 (2018)
F. Marandi, K. Moeini, A. Arkak, Z. Mardani, H. Krautscheid, J. Coord. Chem. 71, 23 (2018)
S. Alyar, Ş Adem, Spectrochem. Acta Part A Mol. Biomol. Spectrosc. 131, 294 (2014)
G.M. Dongare, A.S. Aswar, J. Mol. Struct. 1281, 135107 (2023)
A.A. El-Sherif, M.M. Shoukry, M.M.A. Abd-Elgawad, Spectrochem. Acta Part A Mol. Biomol. Spectrosc. 98, 307 (2012)
R.N. Patel, S.P. Rawat, M. Choudhary, V.P. Sondhiya, D.K. Patel, K.K. Shukla, D.K. Patel, Y. Singh, R. Pandey, Inorg. Chim. Acta 392, 283 (2012)
R.R. Zaky, A.Y. Al-dawood, SILICON 12, 1259 (2020)
Y. Deswal, S. Asija, D. Kumar, D.K. Jindal, G. Chandan, V. Panwar, S. Saroya, N. Kumar, Res. Chem. Intermed. 48, 703 (2022)
A.A. Osowole, A.C. Ekennia, O.O. Olubiyi, M. Olagunju, Res. Chem. Intermed. 43, 2565 (2017)
H. Yakan, T.K. Bakır, M.S. Çavuş, H. Muğlu, Res. Chem. Intermed. 46, 5417 (2020)
Acknowledgements
The authors are greatly acknowledged to the authorities of Sant Gadge Baba Amravati University, Amravati for furnished necessary research facilities viz., Bruker-IR instrument, UV-Vis., and Perkin Elmer-TG analyser. The authors are grateful thanks to SAIF-Punjab University, Chandigarh for elemental, NMR (1H and 13C), HR-Mass spectra and SEM analysis. The authors are also grateful to the sophisticated analytical Instrumental facility of Indian Institute of Technology (IIT)-Mumbai for recording the ESR spectrum and the Principal, Central instrumentation facility, Shri Shivaji Science College, Amravati (M.S.) for powder X-ray diffraction analysis.
Funding
No funding was received from any agencies for this research work.
Author information
Authors and Affiliations
Contributions
GD have been written original draft; utilized software along with the conceptualization; performed formal analysis and investigation. AS contributed in methodology; writing—review and editing; resources as well as in supervision of research work.
Corresponding author
Ethics declarations
Conflict of interest
The authors declares that they have no conflict of interest.
Ethical approval
No animal/ human studies were carried out in the present work.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Dongare, G., Aswar, A. New aroyl heterocyclic (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-4-oxopiperidine-1-carbohydrazide and its metal complexes: synthesis, spectroscopic, thermal, DFT, molecular docking and antimicrobial studies. Res Chem Intermed 50, 745–788 (2024). https://doi.org/10.1007/s11164-023-05169-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-023-05169-2