Synthesis, spectroscopic characterization, antimicrobial evaluation and molecular docking study of novel triazine-quinazolinone based hybrids

Dinari, Mohammad; Gharahi, Fateme; Asadi, Parvin

doi:10.1016/j.molstruc.2017.11.087

Cited by 53 publications

(22 citation statements)

References 28 publications

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“…Triazine‐based ligands have attracted special interest as a result of the importance of these heterocyclic compounds and their various applications, including biological, pharmaceutical, and industrial applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Samy

2020

Applied Organom Chemis

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New mononuclear Fe (III), Cu (II), Ag (I), ZrO ( IV) and UO2(VI) complexes were synthesized by the reaction of metal ions with (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime. The structures of the metal complexes were characterized using analytical, spectral (infrared, electronic, 1H NMR, electron spin resonance (ESR), and mass), magnetic moment, molar conductance, thermal gravimetric analysis, and powder X‐ray diffraction (XRD) measurements. All complexes have octahedral geometries except the Cu (II) complex, which has square planar geometry, and the UO2(VI) complex, in which the coordination number is seven. The ligand acts as a (neutral, monoanionic or dianionic) tridentate with N2O coordinating sites: N‐azomethine, N‐triazine, and O‐oxime. Fluorescence spectral studies were carried out in solid state and in dimethylformamide (DMF). The kinetic parameters of the thermal decomposition stages were calculated using Coats–Redfern equations. The morphological structures of the ligand and some complexes were determined using XRD. The molecular orbital calculations were carried out for the ligand and metal complexes using the Hyperchem 7.52 program on the basis of the PM3 level. The antimicrobial activities of the ligand and its complexes were investigated towards the microorganisms S. aureus and B. subtilis as Gram‐positive bacteria, S. typhimurium and E. coli as Gram‐negative bacteria, C. albicans, and A. fumigatus. The ligand and its complexes showed antitumor activity against Hep G‐2 cell lines, where Cu (II) and Ag (I) complexes seem to be promising as they showed IC50 values that are lower than and comparable to that of the antitumor drug doxorubicin.

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Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Samy

2020

Applied Organom Chemis

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“…SAR analysis of quinazoline‐triazine hybridization led to the discovery of hybrids 46 a‐f , Figure 10. These hybrids displayed potent antimicrobial activity against P. aeruginosa, Escherichia coli , Salmonella entritidis , Listeria monocitogenes , Bacillus subtilis, S. aureus , and C. albicans (Dinari, Gharahi, & Asadi, 2018). In silico analysis of the sulfonamide group containing hybrid molecules validated their ideal accommodation in the active site of DHFR enzyme via H‐bonding interactions with Ile50, Ser49, Phe92, and Gln19 residues in the binding pocket with binding energy of 9.09 kcal/mol.…”

Section: Antimicrobial Properties Of 135‐triazine Based Hybrid Molementioning

confidence: 99%

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

Prasher

Sharma

Aljabali

et al. 2020

Drug Development Research

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Majority of the representative drugs customarily interact with multiple targets manifesting unintended side effects. In addition, drug resistance and over expression of the cellular efflux‐pumps render certain classes of drugs ineffective. With only a few innovative formulations in development, it is necessary to identify pharmacophores and novel strategies for creating new drugs. The conjugation of dissimilar pharmacophoric moieties to design hybrid molecules with an attractive therapeutic profile is an emerging paradigm in the contemporary drug development regime. The recent decade witnessed the remarkable biological potential of 1,3,5‐triazine framework in the development of various chemotherapeutics. The appending of the 1,3,5‐triazine nucleus to biologically relevant moieties has delivered exciting results. The present review focuses on 1,3,5‐triazine based hybrid molecules in the development of pharmaceuticals.

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“…Dinari et al . synthesized a new series of 1,3,5‐triazine incorporating aromatic quinazolinone moieties, and discovered that compound S11 with benzenesulfonamide group showed higher antimicrobial activity with a minimum inhibitory concentration ( MIC ) value of 16 μg/mL, compounds S12 and S13 showed good activity against several tested strains . Asadi et al .…”

Section: Introductionmentioning

confidence: 99%

“…[29] Dinari et al synthesized a new series of 1,3,5-triazine incorporating aromatic quinazolinone moieties, and discovered that compound S11 with benzenesulfonamide group showed higher antimicrobial activity with a minimum inhibitory concentration (MIC) value of 16 lg/mL, compounds S12 and S13 showed good activity against several tested strains. [30] Asadi et al synthesized a series of novel quinazolinone, benzofuran and imidazolium hybrid derivatives, and discovered that compound S14 with two halogen atoms on quinazolinone and benzofuran was the most active against all the tested strains of microorganisms with the MIC value 16 -128 lg/mL, and compound S15 was found to be the most cytotoxic compound against MCF-7 with IC 50 = 0.59 lM among the studied hybrid derivatives. [31] Fleita et al [32] reported several novel thiazole, pyrimidine and benzylidene derivatives derived from quinazoline scaffold, and found that compound S16 and S17 showed remarkable activities against MCF-7 cell line.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Cytotoxic, and Antibacterial Evaluation of Quinazolinone Derivatives with Substituted Amino Moiety

Zhan

et al. 2018

Chemistry & Biodiversity

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A series of novel quinazolinone derivatives containing a substituted amino moiety were synthesized, evaluated for their cytotoxic and antibacterial activities. The results of MTT assay showed that all synthesized target compounds 5A - 5O showed potent cytotoxicity against SGC-7901 (IC , 0.72 - 1.41 μm). Moreover, the compounds 5D, 5I, and 5K showed better selectivity as compared with positive controls pemetrexed and MTX due to weak cytotoxicity against normal tissue cell line HUVSMC. Among synthesized compounds, the compounds 5E, 5J, 5L, and 5N showed broad-spectrum cytotoxic activities against at least four cancer cell lines at a micromolar level. The results of antibacteria evaluation revealed that all synthesized compounds showed good to moderate antibacterial activities against Gram-negative bacteria Escherichia coli. Among them, the MIC values of the compounds 5C, 5F, and 5M were 0.31 μg/mL.

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Synthesis, spectroscopic characterization, antimicrobial evaluation and molecular docking study of novel triazine-quinazolinone based hybrids

Cited by 53 publications

References 28 publications

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

Synthesis, Cytotoxic, and Antibacterial Evaluation of Quinazolinone Derivatives with Substituted Amino Moiety

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