Synthesis of new 5,6-dihydrobenzo[h]quinazoline 2,4-diamino substituted and antiplatelet/antiphlogistic activities evaluation

Brullo, Chiara; Rocca, Massimo; Fossa, Paola; Cichero, Elena; Barocelli, Elisabetta; Ballabeni, Vigilio; Flammini, Lisa; Giorgio, Carmine; Saccani, Francesca; Domenichini, Giuseppe; Bruno, Olga

doi:10.1016/j.bmcl.2011.11.103

Cited by 19 publications

(10 citation statements)

References 24 publications

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“…Infrared (IR) spectra were recorded as KBr pellets on a Fourier transform infrared (FTIR) Nicolet 670 spectrometer and 1 H nuclear magnetic resonance (NMR) spectra were recorded on a Varian GEMINI 200 MHz NMR spectrometer, using tetramethylsilane (TMS) as the internal standard, and chemical shifts were given in δ (ppm). 13 C NMR spectra were obtained on a JEOL EX-400 MHz NMR spectrometer, the chemical shifts are expressed in δ (ppm) using TMS as the internal standard. Mass spectra were obtained from a Shimadzu GCMS-QP-1000 EX spectrometer (70 eV).…”

Section: Methodsmentioning

confidence: 99%

“…This pyrazole intermediate afforded the target arylazo-pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a] pyrimidin-7-ones upon cyclization with 3-piperidinylacrylonitrile, ethyl acetoacetate, ethyl(arylhydrazono)acetoacetates, or (arylhydrazono)propanals. The structures of these compounds were confirmed by 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy, infrared (IR) analysis, and elemental analysis. The disperse colorants produced were applied to printing on polyester fabrics to give satisfactory results.…”

mentioning

confidence: 93%

“…6,7 The reaction of aminopyrazole derivatives with electrophilic reagents affords a variety of fused heterocycles with a broad spectrum of antimicrobial activity. 8–14 Furthermore, these fused heterocycles are also used as intermediates in the dye industry. 15–17 Arylazopyrazolo[1,5-a]pyrimidines were prepared by condensing aminoarylazopyrazoles with β-bifunctional reagents using methodologies initially established in our laboratories.…”

Section: Introductionmentioning

confidence: 99%

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Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Khattab

Elnagdi

Haggaga

et al. 2017

AATCC Journal of Research

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Novel heterocyclic arylazo-disperse dyes containing pyrazolo[1,5-a]pyrimidine structures were prepared via conventional refluxing and microwave heating. Starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamine was obtained from a sequence of reactions. This pyrazole intermediate afforded the target arylazo-pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a] pyrimidin-7-ones upon cyclization with 3-piperidinylacrylonitrile, ethyl acetoacetate, ethyl(arylhydrazono)acetoacetates, or (arylhydrazono)propanals. The structures of these compounds were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy, infrared (IR) analysis, and elemental analysis. The disperse colorants produced were applied to printing on polyester fabrics to give satisfactory results. All the synthesized products were tested as antimicrobial agents. Most compounds exhibited relatively strong antibacterial activity against a panel of Gram-positive and Gram-negative bacteria.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Khattab

Elnagdi

Haggaga

et al. 2017

AATCC Journal of Research

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“…Benzoquinazolines, as the theme of much considerable interest research, have occupied a distinguished position in synthetic-pharmaceutical chemistry, because of their diverse range of pharmacological properties (Al-Salahi et al, 2016, Al-Salahi et al, 2017, Brullo et al, 2012). Several benzo[ h ]-,benzo[ g ]-and benzo[ f ] analogues of quinazolines were found to possess cytotoxic activities and used as tyrosine kinase inhibitors (Huijun, 2017, Nowak et al, 2014, Nowak et al, 2015, Markosyan et al, 2010, Pendergast et al, 1994, Alsaid et al, 2017, Sivalingam et al, 2017, Ghorab et al, 2016, Al-Salahi et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Radioiodination and biodistribution of newly synthesized 3-benzyl-2-([3-methoxybenzyl]thio)benzo[g]quinazolin-4-(3H)-one in tumor bearing mice

Al‐Salahi

Moustapha

Abuelizz

et al. 2018

Saudi Pharmaceutical Journal

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3-Benzyl-2-((3-methoxybenzyl)thio)benzo[g]quinazolin-4(3H)-one was previously synthesized and proved by physicochemical analyses (HRMS, 1H and 13C NMR). The target compound was examined for its radioactivity and the results showed that benzo[g]quinazoline was successfully labeled with radioactive iodine using NBS via an electrophilic substitution reaction. The reaction parameters that affected the labeling yield such as concentration, pH and time were studied to optimize the labeling conditions. The radiochemical yield was 91.2 ± 1.22% and the in vitro studies showed that the target compound was stable for up to 24 h. The thyroid was among the other organs in which the uptake of 125I-benzoquinazoline has increased significantly over the time up to 4.1%. The tumor uptake was 6.95%. Radiochemical and metabolic stability of the benzoquinazoline in vivo/in vitro and biodistribution studies provide some insights about the requirements for developing more potent radiopharmaceutical for targeting the tumor cells.

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“…antimalarial (Nzila et al, 2010;Zhu et al, 2010), antiinflammatory (Brullo et al, 2012) and antimicrobial activities (Ouyang et al, 2006;Yang et al, 2007;German et al, 2008;Rohini et al, 2009;Chevalier et al, 2010). Imatinib, Gefitinib, Erlotinib, and Vandetanib are a series of quinazoline anticancer drugs and have been commercialized and widely used in pharmaceuticals as caner therapy agents.…”

Section: Introductionmentioning

confidence: 99%

Antitumor effect of N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4-amine dihydrochloride on tumor cells in vitro

Huang¹,

Su²,

Wang³

et al. 2012

Afr. J. Pharm. Pharmacol.

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Previous evidence demonstrated the antitumor ability of quinazolines and its derivatives. In this study, the anticancer activities of N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4-amine dihydrochloride against four kinds of cell lines were evaluated by 3-(4,5-dimeth-ylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The bioassay results indicated that title compound possessed wide spectrum of anticancer activity. Androgen-independent prostate cancer (PC-3) cells were employed and microscopic observation, lactate dehydrogenase (LDH) release assay, and Western blot were performed to study the antitumor mechanism of N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4-amine dihydrochloride against tumor cells. It was found that title compound executed anticancer activity in a dose-dependent manner with 24.46 μM IC 50 of 72 h treatment. Microscopic observation and LDH release assay showed that the compound exerted such an effect through antiproliferation pathway rather than cytotoxicity. Furthermore, Western blot analysis revealed that treatment of cells with N-(4-chlorophenyl)-5,6,7trimethoxyquinazolin-4-amine dihydrochloride (at more than 10 μM for 30 min) resulted in an almost complete inhibition of epidermal growth factor (EGF) induced phosphorylation of extracellular signalregulated protein kinase1/2 (ERK1/2) which suggests that its antiproliferation effect is linked to its inhibition of ERK1/2 activation. These data imply that N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4amine dihydrochloride is a potential anticancer agent capable of antiproliferation activity.Key words: N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4-amine dihydrochloride, prostate cancer (PC-3) cell line, antiproliferation, extracellular signal-regulated protein kinase1/2 (ERK1/2).

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Synthesis of new 5,6-dihydrobenzo[h]quinazoline 2,4-diamino substituted and antiplatelet/antiphlogistic activities evaluation

Cited by 19 publications

References 24 publications

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Green Synthesis, Printing Performance, and Antibacterial Activity of Disperse Dyes Incorporating Arylazopyrazolopyrimidines

Radioiodination and biodistribution of newly synthesized 3-benzyl-2-([3-methoxybenzyl]thio)benzo[g]quinazolin-4-(3H)-one in tumor bearing mice

Antitumor effect of N-(4-chlorophenyl)-5,6,7-trimethoxyquinazolin-4-amine dihydrochloride on tumor cells in vitro

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