Synthesis, characterization, cytotoxic screening, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases

Abstract

A series of novel derivatives of quinazolinone Schiff bases were synthesized from benzoic acid starting material and evaluated for potential cytotoxic activities against the human breast adenocarcinoma (MCF-7) and the human colon adenocarcinoma (HT-29) cell lines. Compared to the reference drug, these compounds showed good cytotoxic activities against studied cell lines especially compounds 4d and 4e. The ground-state geometries of these compounds (4a-g) were optimized at the B3LYP/6–31G* density functional theory (DFT) level. Then maximum absorptions electron affinity, ionization potential, electronegativity (χ), energy gap (Egap), hardness (η), softness (S), electrophilicity (ω), and electrophilicity index (ωi) were calculated and discussed. The quantitative structure-activity relationship (QSAR) properties including the physicochemical parameters were also evaluated and studied. The computed properties of our novel synthesized compounds were compared with erlotinib compound.

Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives

“…The antimicrobial activities of the synthesized compounds were studied using broth micro dilution method against three Gram-positive bacteria of Staphylococcus aureus PTCC 1337, Bacillus subtilis PTCC 1023, and Listeria monocitogenes PTCC 1165 and three Gram-negative bacteria including Escherichia coli PTCC 1338, Pseudomonas aeruginosa PTCC 1074, and Salmonella entritidis PTCC 1091 and antifungal activity was screened against Candida albicans PTCC 5027 obtained from Persian Type Culture Collection. Using the micro plate alamar blue assay, minimum inhibitory concentration (MIC) was determined ( 22 23 ).…”

Exploring the interaction between epidermal growth factor receptor tyrosine kinase and some of the synthesized inhibitors using combination of in-silico and in-vitro cytotoxicity methods

“…The cytotoxic activities of synthesized compounds against MCF-7 and HT-29 cell lines were studied by MTT as previously described(2). The cell suspension was treated with 20 μL of various concentrations (0.1-100 μM) of synthesized samples in 1% DMSO diluted with culture medium.…”

“…The experiments were repeated three times. The percentage of cell viability was calculated by reported equation(2). The half maximal inhibitory concentration (IC 50 ) values in μM against both mentioned cell lines are reported in Table 1.…”

“…Epidermal growth factor receptor (EGFR) is the cell-surface receptor of protein tyrosine kinase family which is over-expressed in numerous human tumors, containing ovarian, prostate, breast, bladder, lung, and colon(12). Several quinazoline derivatives such as erlotinib, gefitinib, and lapatinib have been synthesized as reversible inhibitors of tyrosine kinase(3).…”

Structure based design and anti-breast cancer evaluation of some novel 4-anilinoquinazoline derivatives as potential epidermal growth factor receptor inhibitors

“…In recent years, many EGFR inhibitors with different molecular scaffolds have been discovered( 4 5 6 ). Among them, ATP competitive inhibitors of 4-anilinoquinazolines analogs like erlotinib and gefitinib have been approved( 7 8 9 10 ). There are also some reports showing the hopeful benefits from imatinib and combined treatment with a dual inhibitor of EGFR and imatinib( 11 12 ).…”