Synthesis and in vitro antitumor activity of new quinoxaline derivatives

Corona, Paola; Carta, Antonio; Loriga, Mario; Vitale, Gabriella; Paglietti, Giuseppe

doi:10.1016/j.ejmech.2008.07.025

Cited by 96 publications

(64 citation statements)

References 25 publications

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“…Range of growth (%) showed the lowest and the highest growth that was found among different cancer cell lines. For NCI criteria, a compound which reduces the growth of any of the cell line by 32% or less is considered in vitro active [34].…”

Section: In Vitro Anticancer Activitymentioning

confidence: 99%

Design and Synthesis of Benzimidazole Analogs Endowed with Oxadiazole as Selective COX‐2 Inhibitor

Rathore

Rahman

Siddiqui

et al. 2014

Archiv der Pharmazie

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New molecules of benzimidazole endowed with oxadiazole were designed and synthesized from 2-(2-((pyrimidin-2-ylthio)methyl)-1H-benzo[d]imidazol-1-yl)acetohydrazide as 1-((5-substituted alkyl/aryl-1,3,4-oxadiazol-2-yl)methyl)-2-((pyrimidin-2-ylthio)methyl)-1H-benzimidazoles (5a-r) with the aim to acquire selective cyclooxygenase (COX-2) inhibitor activity. The synthesized compounds were screened by in vitro cyclooxygenase assays to determine COX-1 and COX-2 inhibitory potency and the results showed that they had good-to-remarkable activity with an IC50 range of 11.6-56.1 µM. The most active compounds were further screened for their in vivo anti-inflammatory activity by using the carrageenan-induced rat paw edema model. In vitro anticancer activities of the hybrid compounds were assessed by the National Cancer Institute (NCI), USA, against 60 human cell lines, and the results showed a good spectrum. Compound 5l exhibited significant COX-2 inhibition with an IC50 value of 8.2 µM and a percent protection of 68.4%. Compound 5b evinced moderate cytotoxicity toward the UO-31 cell line of renal cancer. A docking study was performed using Maestro 9.0, to provide the binding mode into the binding sites of the cyclooxygenase enzyme. Hopefully, in the future, compound 5l could serve as a lead compound for developing new COX-2 inhibitors.

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Section: In Vitro Anticancer Activitymentioning

confidence: 99%

Design and Synthesis of Benzimidazole Analogs Endowed with Oxadiazole as Selective COX‐2 Inhibitor

Rathore

Rahman

Siddiqui

et al. 2014

Archiv der Pharmazie

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“…The reaction is facile and it is commonly used for synthesizing both quinoxaline and its derivatives (Jang et al 2008). Quinoxalines have shown broad biological activities such as in vitro antitumor activity (Corona et al 2009), antiviral (Rong et al 2007) and anti-inflammatory activity (Burgueteet al 2007); hence, they are an important class of nitrogencontaining heterocycles and useful intermediates in organic synthesis (Corona et al 2009). Recently, some of these types of molecules have been reported as candidates for treatment of cancer and disorders associated with angiogenesis functions (Hazeldine et al 2005).…”

Section: Introductionmentioning

confidence: 98%

A new fluorescence method to analyze water traces in gasoline based on the breakup of diphenylquinoxaline-6-amine–Zn–bis-(2,4,6-trichlorophenyl) oxalate

et al. 2015

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The presence of water in gasoline impairs fuel combustion, corrodes storage tanks and favors microbial proliferation. Therefore, there is a need for simple and sensitive methods to analyze traces of water in gasoline. Here, we developed a method based on the fluorescence of diphenylquinoxaline-6-amine (DPQA). Firstly, DPQA fluorescence is turned off in the presence of bis-(2,4,6-trichlorophenyl) oxalate and zinc perchlorate in anhydrous ethyl acetate. This is explained by the formation of a nonfluorescent complex. Then, adding water at trace levels turns DPQA fluorescence on again, a phenomenon explained by the breakdown of the non-fluorescent complex. We use this method to quantify water in gasoline. Results show an excellent linear correlation with a 0.99 coefficient between fluorescence intensity and water content in the range 0.01-0.2 v/v% with a detection limit of 0.0025 v/ v%. Overall, our findings represent the first application of a turn-on fluorescence sensor to analyze water in gasoline.

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“…The quinoxaline moiety is an important structural motif in the preparation of substances with pronounced biological activities 1 .The quinoxaline core is presented in many drugs with antitumor [2][3] , anticancer 4 , antiamoebic 5 , anticonvulsant 6 , antimalarial 7 , antioxidant 8 and anti-protozoal activity 9 . Some fluorescent dyes 10 , electroluminescent materials…”

Section: Introductionmentioning

confidence: 99%

NANO SbCl5.SiO2: AN EFFICIENT CATALYST FOR THE SYNTHESIS OF QUINOXALINE DERIVATIVES AT ROOM TEMPERATURE UNDER SOLVENTLESS CONDITION

Bamoniri¹,

Mirjalili²,

Karbasizadeh³

2015

J. Chil. Chem. Soc.

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Nano SbCl 5 .SiO 2 as an eco-friendly and efficient nanocatalyst was applied for quinoxaline derivatives preparation with improved yield. In this protocol, α-diketones and 1,2-diamines were condensed in the presence of nanocatalyst at room temperature under solventless conditions. The method gave good yields of quinoxaline derivatives in short reaction times in comparison with earlier methods. Using nontoxic and inexpensive materials, simple work-up, short reaction times and high yields of the products are the advantages of this method.

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Synthesis and in vitro antitumor activity of new quinoxaline derivatives

Cited by 96 publications

References 25 publications

Design and Synthesis of Benzimidazole Analogs Endowed with Oxadiazole as Selective COX‐2 Inhibitor

Design and Synthesis of Benzimidazole Analogs Endowed with Oxadiazole as Selective COX‐2 Inhibitor

A new fluorescence method to analyze water traces in gasoline based on the breakup of diphenylquinoxaline-6-amine–Zn–bis-(2,4,6-trichlorophenyl) oxalate

NANO SbCl5.SiO2: AN EFFICIENT CATALYST FOR THE SYNTHESIS OF QUINOXALINE DERIVATIVES AT ROOM TEMPERATURE UNDER SOLVENTLESS CONDITION

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