ABSTRACT
Six mixed-ligand complexes of Cu(II) were synthesized with quinazolinone Schiff bases (B1-B6) and 2-bromo-7-hydroxy-10,11-dihydroindeno[5,4-c]chromen-6(9H)-one (A), and fully characterized. Their structural attributes were examined through elemental analysis, infrared (IR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy, fast atom bombardment mass spectrometry (FAB-MS), magnetic measurement, and thermal analysis. Additionally, the biological activities of the ligands, complexes, and metal salt were evaluated against microorganisms and compared with standard drugs. The results demonstrated that the newly formed metal complexes displayed significantly elevated biological activities in contrast to the free ligands and metal salt. These findings imply the potential of these mixed-ligand complexes for further advancement as antimicrobial agents.
References
- Alsibaee, A.M., Al-Yousef, H.M., Al-Salem, H.S. (2023). Quinazolinones, the winning horse in drug discovery. Molecules, 28 (2023) 978
- Zhang, J., Liu, J., Ma, Y., Ren, D., Cheng, P., Zhao, J., Zhang, F., Yao, Y. One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety. Bioorganic & Medicinal Chemistry Letters, 26 (2016), 2273-2277
- Radwan, A.A., Alanazi, F.K. Biological activity of quinazolinones. Quinazolinone and Quinazoline Derivatives, (2020), 11.
- Da Silva, C.M., da Silva, D.L., Modolo, L.V., Alves, R.B., de Resende, M.A., Martins, C.V., de Fátima, Â. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2 (2011), 1-8.
- Mir, J.M., Majid, S.A., Shalla, A.H. Enhancement of Schiff base biological efficacy by metal coordination and introduction of metallic compounds as anticovid candidates: a simple overview. Reviews in Inorganic Chemistry, 41 (2021), 199-211.
- Nasab, R.R., Mansourian, M., Hassanzadeh, F. Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives. Research in Pharmaceutical Sciences, 13 (2018), 213-221.
- Verma, S.K., Verma, R., Rakesh, K., Gowda, D.C. Design, synthesis and structure-activity studies of amino acids conjugated quinazolinone-Schiff’s bases as potential antioxidant and anti-inflammatory agents. European Journal of Medicinal Chemistry Reports, 6 (2022), 100087.
- Ashok, U.P., Kollur, S.P., Arun, B.P., Sanjay, C., Suresh, K.S., Anil, N., Baburao, H.V., Markad, D., Castro, J.O., Frau, J. In vitro anticancer activity of 4 (3H)-quinazolinone derived Schiff base and its Cu (II), Zn (II) and Cd (II) complexes: Preparation, X-ray structural, spectral characterization and theoretical investigations. Inorganica Chimica Acta, 511 (2020), 119846.
- Jain, P.K., Joshi, H. Coumarin: chemical and pharmacological profile. Journal of Applied Pharmaceutical Science, (2012), 236-240.
- Tejada, S., Martorell, M., Capo, X., Tur, J.A., Pons, A., Sureda, A. Coumarin and derivates as lipid lowering agents. Current Topics in Medicinal Chemistry, 17 (2017), 391-398.
- Lv, H.-N., Wang, S., Zeng, K.-W., Li, J., Guo, X.-Y., Ferreira, D., Zjawiony, J.K., Tu, P.-F., Jiang, Y. Anti-inflammatory coumarin and benzocoumarin derivatives from Murraya alata. Journal of natural products, 78 (2015), 279-285.
- Vilar, S., Quezada, E., Alcaide, C., Orallo, F., Santana, L., Uriarte, E. Quantitative Structure Vasodilatory Activity Relationship–Synthesis and “In Silico” and “In Vitro” Evaluation of Resveratrol‐Coumarin Hybrids. QSAR & Combinatorial Science, 26 (2007), 317-332.
- Zaki, R.M., Elossaily, Y.A., Kamal El-Dean, A. Synthesis and antimicrobial activity of novel benzo [f] coumarin compounds. Russian Journal of Bioorganic Chemistry, 38 (2012), 639-646.
- Grazul, M., Budzisz, E. Biological activity of metal ions complexes of chromones, coumarins and flavones. Coordination chemistry reviews, 253(2009), 2588-2598.
- Choudhary, S., Kini, S.G., Mubeen, M. Antioxidant activity of novel coumarin substituted benzothiazole derivatives. Der Pharma Chemica, 5 (2013), 213-222.
- Kostova, I. Synthetic and natural coumarins as cytotoxic agents. Current Medicinal Chemistry-Anti-Cancer Agents, 5(1), (2005), 29-46.
- Kharadi, G. Antitubercular and fluorescence studies of copper (II) complexes with quinolone family member, ciprofloxacin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(3), (2011), 898-903.
- Sawant, V., Yamgar, B., Sawant, S., Chavan, S. 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, (2009), 1100-1106.
- Hricovíni, M., Asher, J.R., Hricovíni, M. A study of the photochemical behaviour and relaxation mechanisms of anti–syn isomerisation around quinazolinone–N–N bonds. RSC Advances, 12(50), (2022), 27442-27452.
- Gohil, M.J., Kharadi, G., Ram, S.R. Characterization of mixed ligand Cu (II) complexes through mass spectral, thermal and biological studies. World Scientific News, 182, (2023), 156-178.
- Kharadi, G., Patel, K. Antibacterial, spectral and thermal aspects of drug based‐Cu (II) mixed ligand complexes. Applied Organometallic Chemistry, 23(9), (2009), 391-397.
- Mazej, Z., Arčon, I., Benkič, P., Kodre, A., Tressaud, A. Compressed octahedral coordination in chain compounds containing divalent copper: Structure and magnetic properties of CuFAsF6 and CsCuAlF6. Chemistry – A European Journal, 10(19), (2004), 5052-5058.
- Arne, K., Nielsen, P.H. Infrared spectra of thioamides and selenoamides. Acta Chemica Scandinavica, 20, (1966), 597-629.
- Lemos, F., Muraro, M., Zukerman-Schpector, J., Cavalheiro, E., Dockal, E. Thermal decomposition of complexes. Journal of thermal analysis and calorimetry, 75(2), (2004), 599-606
Download all article in PDF