ABSTRACT
A series of six mixed-ligand complexes of Cu(II) with 7-hydroxy-4-methoxy-10,11-dihydroindeno[5,4-c]chromene-6(9H)-one (A) and Schiff bases derived from quinazolinone (Qn1-Qn6) were synthesized and fully characterized. The structural features of the complexes were investigated using various spectroscopic techniques, including elemental analysis, infrared (IR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy, fast atom bombardment mass spectrometry (FAB-MS), magnetic measurement, and thermal studies. Furthermore, the biological activities of the ligands, complexes, and metal salt were assessed in vitro against both gram-positive and gram-negative microorganisms. The results showed that the newly synthesized metal complexes exhibited significantly higher biological activities compared to the free ligands and metal salt. These findings suggest that the mixed-ligand complexes have potential for further development as antimicrobial agents.
References
- El-Sonbati, A., El-Mogazy, M., Nozha, S., Diab, M., Abou-Dobara, M., Eldesoky, A., & Morgan, S. M. Mixed ligand transition metal (II) complexes: Characterization, spectral, electrochemical studies, molecular docking and bacteriological application. Journal of Molecular Structure, 1248 (2022) 131498
- Manikandamathavan, V. M., Parameswari, R. P., Weyhermüller, T., Vasanthi, H. R., & Nair, B. U. Cytotoxic copper (II) mixed ligand complexes: Crystal structure and DNA cleavage activity. European Journal of Medicinal Chemistry, 46(10) (2011) 4537-4547.
- Mann, M., Hendrickson, R. C., & Pandey, A. Analysis of proteins and proteomes by mass spectrometry. Annual Review of Biochemistry, 70 (2001) 437-473
- Zoubi, W. A., Al-Hamdani, A. A. S., & Ko, Y. G. Schiff bases and their complexes: Recent progress in thermal analysis. Journal of Saudi Chemical Society, 21(9) (2017) 1052-1069
- Noor, N., & Isa, M. J. Investigation on transport and thermal studies of solid polymer electrolyte based on carboxymethyl cellulose doped ammonium thiocyanate for potential application in electrochemical devices. Solid State Ionics, 344 (2019) 44-53
- Singh, A. R., & Kalirajan, K. J. Anti-microbial activity of turmeric natural dye against different bacterial strains. Journal of Applied Pharmaceutical Science, 2(2) (2012) 210-212
- You, Z., Ran, X., Dai, Y., & Ran, Y. Clioquinol, an alternative antimicrobial agent against common pathogenic microbe. Journal of Drug Delivery Science and Technology, 28(2018) 492-501
- Kharadi, G. J. Effect of the thermal decomposition and in vitro antimicrobial activity of mixed ligand copper (II) complexes. Journal of Saudi Chemical Society, 16(4) (2012) 424-431
- Zhang, J., Cheng, P., Ma, Y., Liu, J., Miao, Z., Ren, D., Fan, C., & Liang, M. An efficient nano CuO-catalyzed synthesis and biological evaluation of quinazolinone Schiff base derivatives and bis-2,3-dihydroquinazolin-4(1H)-ones as potent antibacterial agents against Streptococcus lactis. Tetrahedron Letters, 57(48) (2016) 5271-5277
- Prabhala, P., Sutar, S. M., Savanur, H. M., Joshi, S. D., & Kalkhambkar, R. G. In vitro antimicrobial combat, molecular modelling and structure-activity relationship studies of novel class of aryl-ethyne tethered coumarin analogues and some 3-aryl coumarin derivatives. European Journal of Medicinal Chemistry: Chemistry and Biology, 5(2022) 100048
- Nasab, R. R., Mansourian, M., & Hassanzadeh, F. J. Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives. Research on Pharmaceutical Sciences, 13(3) (2018) 213-223
- Siddappa K, Mane SB, Manikprabhu D. Spectral characterization and 3D molecular modeling studies of metal complexes involving the O, N-donor environment of quinazoline-4(3H)-one Schiff base and their biological studies. Scientific World Journal. 2014 Feb 11; 2014: 817365. doi: 10.1155/2014/817365
- Gatadi, S., Lakshmi, T. V., & Nanduri, S. J. 4(3H)-Quinazolinone derivatives: Promising antibacterial drug leads. Saudi Pharmaceutical Journal, 27(2) (2019) 157-172.
- Kharadi, G. J. Antitubercular and fluorescence studies of copper (II) complexes with quinolone family member, ciprofloxacin. Journal of Saudi Chemical Society, 15(4) (2011) 389-398
- Sawant, V., Yamgar, B., Sawant, S., & Chavan, S. J. Synthesis, structural characterization, thermal and electrochemical studies of mixed ligand Cu (II) complexes containing 2-phenyl-3-(benzylamino)-1,2-dihydroquinazoline-4-(3H)-one and bidentate N-donor ligands. Journal of Saudi Chemical Society, 13(4) (2009) 321-329
- Hricovíni, M., Asher, J. R., & Hricovíni, M. J. A study of the photochemical behaviour and relaxation mechanisms of anti-syn isomerisation around quinazolinone-N-N bonds. Journal of Molecular Structure, 1290 (2022) 27442-27452.
- Kharadi, G. J., & Patel, J. A. Antibacterial, spectral and thermal aspects of drug-based Cu (II) mixed ligand complexes. Journal of Saudi Chemical Society, 13(5) (2009) 391-397
- Dodsworth, E. S., & Lever, A. J. The use of optical electronegativities to assign electronic spectra of semiquinone complexes. Coordination Chemistry Reviews, 101 (1990) 151-157
- Arish, D., & Nair, M. S. Synthesis, characterization and biological studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes with pyrral-l-histidinate. Advances in Bioresearch, 5(3) (2012) 179-186
- Ismail, T. M. Mononuclear and binuclear Co (II), Ni (II), Cu (II), Zn (II) and Cd (II) complexes of Schiff-base ligands derived from 7-formyl-8-hydroxyquinoline and diaminonaphthalenes. Journal of Coordination Chemistry, 58(2) (2005) 141-151.
- Kharadi, G., Patel, J., & Dholakiya, B. Antituberculosis, antifungal and thermal activity of mixed ligand transition metal complexes. Journal of Saudi Chemical Society, 14(4) (2010) 369-377
- Panchal, P. K., Patel, M. J., & Kalkhambkar, R. G. Synthesis, structural characterization, and antibacterial studies of some mixed-ligand first row d-transition metal complexes. Journal of Inorganic and Organometallic Polymers and Materials, 14(4) (2004) 327-340.
- Yao, F., Wu, Q., Lei, Y., & Guo, W. Stability, Thermal decomposition kinetics of natural fibers: activation energy with dynamic thermogravimetric analysis. Journal of Polymers and the Environment, 16(2) (2008) 90-98.
- Kharadi, G. J., & Chavan, S. J. Calorimetry, Molar conductance, magnetic susceptibility, mass spectra, and thermal decomposition studies on Cu (II) compounds with substituted terpyridines and clioquinol drug. Journal of Saudi Chemical Society, 18(4) (2014) 333-341.
- Sleno, L. J. The use of mass defect in modern mass spectrometry. Journal of the American Society for Mass Spectrometry, 23(9) (2012) 1511-1521.
- Baluja, S., Solanki, A., & Kachhadia, N. J. Evaluation of biological activities of some Schiff bases and metal complexes. Journal of the Serbian Chemical Society, 71(3) (2006) 295-301.
- Chauhan, G., Kharadi, G. J., & Patel, K. J. Synthesis, spectroscopic and in-vitro antifungal studies of drug-based mixed ligand complexes. Journal of Saudi Chemical Society, 14(4) (2010) 345-355
- Surbhi V. Upadhyay, Raksha V. Zala, Keyur D. Bhatt, Synthesis, characterization, biological activity of Schiff bases derived from 2-bromo-4-methyl aniline and its potentiometric studies with Cu(II), Co(II) and Ni(II) ions. World Scientific News 145 (2020) 1-15
- Jalpa V. Chopda, Jignesh P. Patel, Parsotam H. Parsania, Synthesis and spectral analysis of (E)-1-(2,4-dihydroxy phenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one. World News of Natural Sciences 46 (2023) 46-52
- K. Joshi, N. M. Dodia, D. M. Purohit, Synthesis and antimicrobial activity of {2-amino/2-methoxy}-4-(2’-n-butyl-4’-chloro-1’-H-imidazol-5’-yl)-6-aryl nicotinonitriles. World News of Natural Sciences 43 (2022) 76-82
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