Synthesis of New Quinazoline Derivatives

Baitiche, Milad; Mahamoud, Abdallah; Benachour, Djafer; Merbah, M.; Barbe, Jacques

doi:10.1515/hc.2004.10.4-5.269

Cited by 7 publications

(4 citation statements)

References 10 publications

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“…Synthetic pathway for the production of alkylaminoquinazoline compounds. The synthesis of the various quinazoline derivatives has been reported previously (Baitiche et al, 2004). The structures of the compounds tested are shown together with their identification number (BG).…”

Section: Resultsmentioning

confidence: 99%

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An alkylaminoquinazoline restores antibiotic activity in Gram-negative resistant isolates

et al. 2011

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To date, various bacterial drug efflux pump inhibitors (EPIs) have been described. They exhibit variability in their activity spectrum with respect to antibiotic structural class and bacterial species. Among the various 4-alkylaminoquinazoline derivatives synthesized and studied in this work, one molecule, 1167, increased the susceptibility of important human-pathogenic, resistant, Gram-negative bacteria towards different antibiotic classes. This 4-(3-morpholinopropylamino)-quinazoline induced an increase in the activity of chloramphenicol, nalidixic acid, norfloxacin and sparfloxacin, which are substrates of the AcrAB-TolC and MexAB-OprM efflux pumps that act in these multidrug-resistant isolates. In addition, 1167 increased the intracellular concentration of chloramphenicol in efflux pump-overproducing strains. The rate of restoration depended on the structure of the antibiotic, suggesting that different sites in the efflux pumps may be involved. A molecule exhibiting a morpholine functional group and a propyl extension of the side chain was more active.

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Section: Resultsmentioning

confidence: 99%

“…Compounds were characterized by NMR spectrometry ( 1 H and 13 C NMR). Details of the synthesis and the purification process have been reported previously (Baitiche et al, 2004).…”

Section: Methodsmentioning

confidence: 99%

An alkylaminoquinazoline restores antibiotic activity in Gram-negative resistant isolates

et al. 2011

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“…The quinazoline derivatives, labelled BG1189 and BG1190, studied in this paper were designed as EPIs at UMR-MD1, Facultés de Médecine et de Pharmacie, Université de la Méditerranée, Marseille, France. The chemical synthesis of these derivatives was reported in [ 45 ].…”

Section: Methodsmentioning

confidence: 99%

Quinazoline Derivatives Designed as Efflux Pump Inhibitors: Molecular Modeling and Spectroscopic Studies

et al. 2021

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Multidrug resistance of bacteria is a worrying concern in the therapeutic field and an alternative method to combat it is designing new efflux pump inhibitors (EPIs). This article presents a molecular study of two quinazoline derivatives, labelled BG1189 and BG1190, proposed as EPIs. In silico approach investigates the pharmacodynamic and pharmacokinetic profile of BG1189 and BG1190 quinazolines. Molecular docking and predicted ADMET features suggest that BG1189 and BG1190 may represent attractive candidates as antimicrobial drugs. UV-Vis absorption spectroscopy was employed to study the time stability of quinazoline solutions in water or in dimethyl sulfoxide (DMSO), in constant environmental conditions, and to determine the influence of usual storage temperature, normal room lighting and laser radiation (photostability) on samples stability. The effects of irradiation on BG1189 and BG1190 molecules were also assessed through Fourier-transform infrared (FTIR) spectroscopy. FTIR spectra showed that laser radiation breaks some chemical bonds affecting the substituents and the quinazoline radical of the compounds.

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“…Quinazoline structure was fully described; a series of quinazoline derivatives were developed at UMR-MD1 (Marseille, France) [4]. Among them, 3-[2-(dimethylamino) ethyl]-6-nitroquinazolin-4(3H)-one is considered for stability studies in the present paper.…”

Section: Introductionmentioning

confidence: 99%

Time Stability Studies of Quinazoline Derivative Designed to Fight Drug Resistance Acquired by Bacteria

Militaru¹,

Smarandache²,

Mahamoud³

et al. 2011

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The 3-[2-(dimethylamino)ethyl]-6-nitroquinazolin-4(3H)-one (BG1188) may modify the antibiotic susceptibility of human Gram-negative bacteria which present multidrug resistant phenotype. This application requires to know the time stability of BG1188 solutions. This paper reports for the first time about the time stability of the BG1188 solutions measured by optical absorption; the solvents were ultrapure de-ionized water and dimethyl sulfoxide (DMSO). In ultrapure water, BG1188 concentration varied between 2x10 -3 M (stock solution) and 10 -6 M, at pH = 6.7. In DMSO, the concentration was 10 -3 M (recommended by higher activity on bacteria). Solutions in ultrapure water were kept in dark at 4°C and measured at room temperature (22°C). The ultraviolet-visible (UV-Vis) absorption spectra have shown that only monomer forms were present in solutions. One of the obtained results is that the time evolution of the absorption spectra at 10 -3 M in ultrapure water shows a reproducibility within the measuring errors (±1.045%) for time intervals up to 1032 hours (more than 40 days) after preparation, showing a high stability of BG1188 solutions; generally, samples are stable within the experimental errors at concentrations higher than 10 -5 M, but the stability time interval may be variable: from 119 days at 10 -4 M to 34 days at 10 -5 M.As for solutions in the DMSO, the absorption spectra show that the samples exhibit modifications immediately after preparation, in terms of peak intensities and shapes, so that the BG1188 solutions in DMSO may be considered as unstable.

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Synthesis of New Quinazoline Derivatives

Cited by 7 publications

References 10 publications

An alkylaminoquinazoline restores antibiotic activity in Gram-negative resistant isolates

An alkylaminoquinazoline restores antibiotic activity in Gram-negative resistant isolates

Quinazoline Derivatives Designed as Efflux Pump Inhibitors: Molecular Modeling and Spectroscopic Studies

Time Stability Studies of Quinazoline Derivative Designed to Fight Drug Resistance Acquired by Bacteria

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