Solvent-free Synthesis, Characterization and Biological Activity of Transition Metal Complexes of Schiff Base Ligand Derived (E)-N'-((1H-indol-3-yl) methylene)-4-chlorobenzohydrazide

Authors

  • Sadashiv N. Sinkar Department of Chemistry, MSS’S Arts, Science and Commerce College Ambad, Dist. Jalna, Maharashtra, India Author

DOI:

https://doi.org/10.32628/IJSRST251353

Keywords:

Microwave irradiation, Benzohydrazide, Thermal Study, Novel Schiff Base Ligand, Antibacterial Activity

Abstract

The present study explores the microwave-assisted synthesis, characterization, and biologicalactivity of transition metal complexes of a Schiff base ligand derived from (E)-N'-((1H-indol-3-yl)methylene)-4-chlorobenzohydrazide. The ligand and its metal complexes were synthesized using an eco-friendly microwave irradiation method to enhance reaction efficiency and yield. Metal complexes were derived from nitrate of Co(II), Ni(II), Cu(II), Zn(II), salts with novel ligand at the end of the reaction all metal complexes show fine colour. By TLC and melting point of each complex was confirming the formation of metal complex. The synthesized compounds were characterized by various spectroscopic techniques, including FT-IR, UV-Vis, NMR, and elemental analysis. The metal complexes were further analyzed using Infrared spectroscopy, UV-visible spectroscopy and thermogravimetric analysis. The antibacterial activities of the Schiff base ligand and its metal complexes were tested against Escherichia coli, Staphylococcus aurous and Salmonella Typhi.

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References

Kumar, S.S.; Biju, S.; Sadasivan, V. Synthesis, structure characterization and biological studies on a new aromatic hydrazone, 5-(2-(1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H- pyrazol-4-yl) hydrazono)-2, 2-dimethyl-1, 3-dioxane - 4, 6-dione, and its transition metal complexes. Journal of Molecular Structure 2018, 1156,201209, https://doi.org/10.1016/j.molstruc.2017.11.057. DOI: https://doi.org/10.1016/j.molstruc.2017.11.057

Aly, M.M.; Mohamed, Y.A.; El-Bayouki, K.A.; Basyouni, W.M.; Abbas, S.Y. Synthesis of some new 4 (3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities-Part-1. European Journal of Medicinal Chemistry, 2010, 45, 3365-3373. https://doi.org/10.1016/j.ejmech.2010.04.020. DOI: https://doi.org/10.1016/j.ejmech.2010.04.020

Ramaiah, K.; Prashanth, J.; Haribabu, J.; Srikanth, K.E.; Reddy, B.V.;Karvembu, R.; Reddy, K.L. Vibrational spectroscopic (FT-IR, FT-Raman), anti-inflammatory, docking and molecular characteristic studies of Ni (II) complex of 2-aminonicotinaldehyde using theoretical and experimental methods. Journal of Molecular Structure 2019,5,769-781,https://doi.org/10.1016/j.molstruc.2018.08.044. DOI: https://doi.org/10.1016/j.molstruc.2018.08.044

Sanivarapu, S.; Vaddiraju, N.; Velide, L. Synthesis and anti-inflammatory activity of 1, 2-3-substituted 2a1, 4, 5-triazacyclopenta [cd] indene derivatives. Medicinal Chemistry Research 2019, 28, 1461-1470, https://doi.org/10.1007/s00044-019-02386-6. DOI: https://doi.org/10.1007/s00044-019-02386-6

Negalurmath, V.S.; Boa, S.K.; Kotresh, O.; Lakshmi, P.A.; Basanagouda, M. Benzofuran-oxadiazole hybrids: Design, synthesis, antitubercular activity and molecular docking studies. Chemical Data Collections2019,1, https://doi.org/10.1016/j.cdc.2019.100178.

Concha, C.; Quintana, C.; Klahn, A.H.; Artigas, V.; Fuentealba, M.; Biot, C.; Halloum, I.; Kremer, L.; López, R.; Romanos, J.; Huentupil, Y. Organometallic tosyl hydrazones: Synthesis, characterization, crystal structures and in vitro evaluation for anti-mycobacterium tuberculosis and antiproliferative activities.Polyhedron2017,131,40-45, https://doi.org/10.1016/j.poly.2017.04.031. DOI: https://doi.org/10.1016/j.poly.2017.04.031

Mirams, R.E.; Smith, S.J.; Hadler, K.S.; Ollis, D.L.; Schenk, G.; Gahan, L.R. Cadmium (II) complexes of the glycerophosphodiester-degrading enzyme GpdQ and a biomimetic N, O ligand. Journal of Biological Inorganic Chemistry 2008, 13, 1065-1072, https://doi.org/10.1007/s00775-008-0392-5. DOI: https://doi.org/10.1007/s00775-008-0392-5

Turan, N.; Buldurun, K.; Çolak, N.; Özdemir, İ. Preparation and spectroscopic studies of Fe(II), Ru(II), Pd(II) and Zn(II) complexes of Schiff base containing terephthalaldehyde and their transfer hydrogenation and Suzuki-Miyaura coupling reaction. Open Chemistry 2019, 17, 571-580, https://doi.org/10.1515/chem2019-0074. DOI: https://doi.org/10.1515/chem-2019-0074

Vinusha, H.; Prasad, S.; Ramu, R.; Shirahatti, P.; Prasad, N.; Begum, M. Chemical Synthesis, Spectral Characterization and Biological Investigations of Novel Triazole-Based Schiff Base Ligand and its Transition Complexes. Letters in Applied NanoBioScience 2020, 9, 1372-1388, https://doi.org/10.33263/LIANBS93.13721388. DOI: https://doi.org/10.33263/LIANBS93.13721388

Ambika, S.; Manojkumar, Y.; Arunachalam, S.; Gowdhami, B.; Meenakshi Sundaram, K.K.; Solomon, R.V.; Venuvanalingam, P.; Akbarsha, M.A.; Sundararaman, M. Biomolecular Interaction, Anti-Cancer and Anti-Angiogenic Properties of Cobalt(III) Schiff Base Complexes. Scientific Reports 2019, 9, 1-14, https://doi.org/10.1038/s41598-019-39179-1. DOI: https://doi.org/10.1038/s41598-019-39179-1

Liu, F.; Jin, P.; Gong, H.; Sun, Z.; Du, L.; Wang, D. Antibacterial and Antibiofilm Activities of Thyme Oil [against Foodborne Multiple Antibiotics-Resistant Enterococcus Faecalis. Poult. Sci. 2020, 99, 5127–5136, doi:10.1016/j.psj.2020.06.067. 10. DOI: https://doi.org/10.1016/j.psj.2020.06.067

Azkiyah, S.Z. Pengaruh Uji Antibakteri Ekstrak Rimpang Jahe Terhadap Pertumbuhan Staphylococcus Aureus Dan Escherichia coli Secara In Vitro. J. Farm. Tinctura 2020, DOI: https://doi.org/10.35316/tinctura.v1i2.1003

Song, Y.J.; Yu, H.H.; Kim, Y.J.; Lee, N.-K.; Paik, H.-D. Anti-Biofilm Activity of Grapefruit Seed Extract against Staphylococcus Aureus and Escherichia coli. J. Microbiol. Biotechnol. 2019,29,1177-1183, doi:10.1041/jmb.1905.05022. DOI: https://doi.org/10.4014/jmb.1905.05022

Kim, S.-Y.; Kang, S.-S. Anti-Biofilm Activities of Manuka Honey against Escherichia coli O157:H7. Food Sci. Anim. Resour.2020,40,668–674, doi:10.5851/kosfa.2020.e42. DOI: https://doi.org/10.5851/kosfa.2020.e42

Obied, H.N.; AL-Zobaidy, M.A.-H.; Hindi, N.K.K. An in Vitro Study of Anti-Bacterial, Anti-Adherence, Anti- Biofilm and Anti-Motility Activities of the Aqueous Extracts of Fresh and Powdered Onion (Allium Cepa) and Onion Oil. J Pharm Sci 2018, 10,7.

Hamzah, H.; Yudhawan, I.; Rasdianah, N.; Setyowati, E.; Nandini, E.; Utami, S. Clove Oil Has the Activity to Inhibit Middle , Maturation and Degradation Phase of Candida Tropicalis Biofilm Formation. Biointerface Reserch Appl. Chem. 2022, 12, 1507–1519. DOI: https://doi.org/10.33263/BRIAC122.15071519

Sharma, G. Characterization Of Antimicrobial Substance With Antibiofilm Activity From PediococcusAcidilactici.J.Microbiol.Biotechnol.FoodSci.2020,9,979–982, doi:10.15414/jmbfs.2020.9.5.979-982. DOI: https://doi.org/10.15414/jmbfs.2020.9.5.979-982

Prasad, K.S.; Pillai, R.R.; Shivamallu, C.; Prasad, S.K.; Jain, A.S.; Pradeep, S.; Armaković, S.; Armaković, S.J.; Srinivasa, C.; Kallimani, S.; Amachawadi, R.G.; Ankegowda, V.M.; Marraiki, N.; Elgorban, A.M.; Syed, A. Tumoricidal Potential of Novel Amino-1,10-phenanthroline Derived Imine Ligands: Chemical Preparation, Structure, and Biological Investigations. Molecules 2020, 25, 2865-2877, https://doi.org/10.3390/molecules25122865. DOI: https://doi.org/10.3390/molecules25122865

Negalurmath, V.S.; Boa, S.K.; Kotresh, O.; Lakshmi, P.A.; Basanagouda, M. Benzofuran-oxadiazole hybrids: Design, synthesis, antitubercular activity and molecular docking studies.Chemical Data Collections 2019, 1, https://doi.org/10.1016/j.cdc.2019.100178. https://doi.org/10.1016/j.jinorgbio.2019.02.003. DOI: https://doi.org/10.1016/j.cdc.2019.100178

Bellamy, L. The Infrared Spectra of Complex Molecules, Second ed., Chapman & Hall, Methuen, London, (1958).

Nakamoto, K. Infrared Spectra of Inorganic and Coordination Compounds, Part B, Fifth ed.,Wiley Interscience, New York, (1971).

Subbaraj,P., Ramu, A., Raman, N., Dharmaraja, J. Synthesis, characterization, DNA interaction and pharmacological studies of substituted benzophenone derived Schiff base metal (II) complexes, Journal of Saudi Chemical Society., 19: 207–216 (2015). DOI: https://doi.org/10.1016/j.jscs.2014.05.002

Karampurwala A, Ray A, Patel R. Polychelates of Bis-Semi carbazone of 5,5′-Methylene Bis-Salicylaldehyde with VO2+, Mn(II), Cr(III), Fe(III), and Zn(II). Synth Reactivity, Inorg Met Org Chem., 19: 219-234 (1989). DOI: https://doi.org/10.1080/00945718908048065

Pranita, U., Gawande, Mandlik, P., Aswar, A. Synthesis and characterization of Cr(III), Mn(III), Fe(III), VO(IV), Zr(IV) and UO2(VI) complexes of Schiff base derived from isonicotinoyl hydrazine, Indian J Pharm Sci., 77(4): 376-381 (2015). DOI: 10.4103/0250-474X.164779 DOI: https://doi.org/10.4103/0250-474X.164779

Lever, A. Inorganic Electronic Spectroscopy, Elsevier publishing Co.Ltd. New York, (1984).

Ray, M., Bhattacharya, R., Chaudhuri, S., Righi, L., et al. Polyhedron., 22: 617-625 (2003). DOI: https://doi.org/10.1016/S0277-5387(02)01435-3

Zayed, M., Nour, F., Dien, E., Mohamed, G., El-Gamal, N. Spectrochim. Acta part A.,60: 2843-2852 (2004). DOI: https://doi.org/10.1016/j.saa.2003.12.051

Shirodkar, S., Mane, P., Chondhekar, T. Synthesis and fungitoxic studies of Mn(II), Co(II), Ni(II) and Cu(II) with some heterocyclic Schiff base ligands, Indian J. Chem., 40: 1114-1117 (2001).

M., Levent, A., Ekerci, M. Synthesis, characterization, and thermal investigation of some metal complexes containing polydentate ONO-donor heterocyclic Schiff base ligand, Russ. J. Coord. Chem., 30: 695–699 (2004). DOI: https://doi.org/10.1023/B:RUCO.0000040726.57728.a3

Guidote, A., Ando, J., Kurusu, Y., Nagao, H., Masuyama, Y. Inorg. Chim. Acta., 314: 27-35 (2001). DOI: https://doi.org/10.1016/S0020-1693(01)00294-8

Zeyrek, C., Elmali, A., Elerman, Y., Svoboda, I. Z.Naturforsch., 60b: 143-150(2005). DOI: https://doi.org/10.1515/znb-2005-0203

Patil, R. Acta Poioniac Pharmaceutica-Drug Research., 64: 345-353 (2007).

Brandt, C., Kitchen, J., Beckmann, U., White,N., Jameson, G., Brooker, S.SupramolecularChemistry., 19: 17-26 (2007).

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Published

30-07-2025

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Research Articles

How to Cite

Solvent-free Synthesis, Characterization and Biological Activity of Transition Metal Complexes of Schiff Base Ligand Derived (E)-N’-((1H-indol-3-yl) methylene)-4-chlorobenzohydrazide. (2025). International Journal of Scientific Research in Science and Technology, 12(4), 772-778. https://doi.org/10.32628/IJSRST251353