ABSTRACT
Six Cu(II) mixed-ligand complexes were synthesized using 5-hydroxy-8,9-dihydrobenzo[f]indeno[5,4-c]chromen-4(7H)-one (L) and quinazolinone Schiff bases (B1-B6). These complexes were fully characterized through various techniques, including elemental analysis, infrared (IR) spectroscopy, proton nuclear magnetic resonance (1H-NMR) spectroscopy, fast atom bombardment mass spectrometry (FAB-MS), magnetic measurement, and thermal analysis. Furthermore, the biological activities of these ligands, complexes, and metal salt were evaluated against microorganisms and compared with standard drugs. The results revealed that the newly formed metal complexes exhibited significantly elevated biological activities compared to the free ligands and metal salt. These findings suggest the potential of these mixed-ligand complexes for further advancement as antimicrobial agents.
References
- Bhatia, R., et al., Metal-catalyzed synthetic strategies toward coumarin derivatives. Chemistry of Heterocyclic Compounds, 54(4), (2018) 280-291
- Jain, P.K. and H. Joshi, Coumarin: chemical and pharmacological profile. Journal of Applied Pharmaceutical Science, (2012), 236-240
- Stringlis, I.A., R. De Jonge, and C.M. Pieterse, The age of coumarins in plant–microbe interactions. Plant and Cell Physiology, 60(7), (2019) 1405-1419
- Aslam, K., et al., Short communication: synthesis and applications of Coumarin. J. Pharm. Sci, 23(4), (2010), 449-454
- Kostova, I., Studying plant-derived coumarins for their pharmacological and therapeutic properties as potential anticancer drugs. Expert opinion on drug discovery, 2(12), (2007), 1605-1618
- Srikrishna, D., C. Godugu, and P.K. Dubey, A review on pharmacological properties of coumarins. Mini reviews in medicinal chemistry, 18(2), (2018), 113-141
- Choudhary, S., S.G. Kini, and M. Mubeen, Antioxidant activity of novel coumarin substituted benzothiazole derivatives. Der Pharma Chemica, 5(4), (2013), 213-222
- Patel, G. and S. Banerjee, Review on synthesis of bio-active coumarin-fused heterocyclic molecules. Current Organic Chemistry, 24(22), (2020) 2566-2587.
- Nasab, N.H., et al., Acetylcoumarin in cyclic and heterocyclic-containing coumarins: Synthesis and biological applications. Tetrahedron, 129, (2022), 133158.
- Connolly, D.J., et al., Synthesis of quinazolinones and quinazolines. Tetrahedron, 61(43), (2005), 10153-10202.
- Khan, I., et al., Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: The advances continue. European journal of medicinal chemistry, 90, (2015), 124-169.
- Rajput, R. and A.P. Mishra, A review on biological activity of quinazolinones. International Journal of Pharmacy and Pharmaceutical Sciences, 4(2), (2012), 66-70.
- Jain, A., S. De, and P. Barman, Microwave-assisted synthesis and notable applications of Schiff-base and metal complexes: a comparative study. Research on Chemical Intermediates, 48(5), (2022), 2199-2251.
- Ullas, B., et al., Multi-targeted quinazolinone-Schiff’s bases as potent bio-therapeutics. Results in Chemistry, 2, (2020), 100067.
- Ubale, P., et al., Evaluation of in vitro anticancer, antimicrobial and antioxidant activities of new Cu (II) complexes derived from 4 (3H)-quinazolinone: Synthesis, crystal structure and molecular docking studies. Journal of Molecular Structure, 1251, (2022), 131984.
- Kharadi, G., Antitubercular and fluorescence studies of copper (II) complexes with quinolone family member, ciprofloxacin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(5), (2011), 898-903.
- Sawant, V., et al., 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. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74(5), (2009), 1100-1106.
- Hricovíni, M., J.R. Asher, and M. Hricovíni, A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone–N–N [double bond, length as m-dash] bonds. RSC advances, 12(42), (2022), 27442-27452.
- Kharadi, G. and K. Patel, Antibacterial, spectral and thermal aspects of drug based‐Cu (II) mixed ligand complexes. Applied Organometallic Chemistry, 23(10), (2009), 391-397.
- Hatfield, W.E. and T. Piper, Spectral and magnetic properties of chlorocuprates. Inorganic Chemistry, 3(6), (1964), 841-843.
- Sundaraganesan, N., B. Anand, and B.D. Joshua, FTIR, FT-raman spectra and ab initio DFT vibrational analysis of 2, 4-dichloro-6-nitrophenol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 65(5), (2006), 1053-1062.
- Lothenbach, B., P. Durdzinski, and K. De Weerdt, Thermogravimetric analysis. A practical guide to microstructural analysis of cementitious materials, 1 (2016), 177-211. CRC Press. eBook ISBN 9781351228497
Download all article in PDF