Synthesis and anticancer activity evaluation of new 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethyl-quinoxaline 1,4-di-N-oxide derivatives

Zarranz, Belén; Jaso, Andrés; Aldana, Ignacio; Monge, Antonio

doi:10.1016/j.bmc.2004.04.013

Cited by 99 publications

(70 citation statements)

References 10 publications

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“…In most cases, the 7-substituted isomer prevailed over 6-substituted isomer, and when the methoxy substituted quinoxalines were prepared, only the 7-isomer was obtained, as previously described. [29,30] …”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives

Moreno

Ancizu

Pérez‐Silanes

et al. 2010

European Journal of Medicinal Chemistry

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Abstract:As a continuation of our research and with the aim of obtaining new antituberculosis agents which can improve the current chemotherapeutic antituberculosis treatments, forty-three new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis strain H 37 Rv. Active compounds were also screened to assess toxicity to a VERO cell line. Results indicate that compounds with a methyl moiety substituted in position 3 and un-substituted benzyl substituted on the carboxamide group provide an efficient approach for further development of antituberculosis agents.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives

Moreno

Ancizu

Pérez‐Silanes

et al. 2010

European Journal of Medicinal Chemistry

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“…[1][2][3][4][5][6] In fact, the quinoxaline 1,4-dioxides are a group of synthetic antibacterial agents largely used as medicinal feed additives 7,8 and they are also used as bioreductive cytotoxic agents/species. [9][10][11] Several compounds derived from quinoxaline 1,4-dioxide, which were activated under hypoxic conditions, are at different stages of development to be used as drugs. These compounds are thought to be active due to the creation of cytotoxic radicals formed after N-O bond cleavage taking place in these N-dioxide compounds.…”

Section: Introductionmentioning

confidence: 99%

Energetic and structural characterization of 2‐R‐3‐methylquinoxaline‐1,4‐dioxides (R = benzoyl or tert‐butoxycarbonyl): experimental and computational studies

Gomes

Sousa

Gonçalves

et al. 2007

J of Physical Organic Chem

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The gaseous standard molar enthalpies of formation of two 2-R-3-methylquinoxaline-1,4-dioxides (R ¼ benzoyl or tert-butoxycarbonyl), at T ¼ 298.15 K, were derived using the values for the enthalpies of formation of the compounds in the condensed phase, measured by static bomb combustion calorimetry, and for the enthalpies of sublimation, measured by Knudsen effusion, using a quartz crystal oscillator. The three dimensional structure of 2-tert-butoxycarbonyl-3-methylquinoxaline-1,4-dioxide has been obtained by X-ray crystallography showing that the two N-O bond lengths in this compound are identical. The experimentally determined geometry in the crystal is similar to that obtained in the gas-phase after computations performed at the B3LYP/6-311 þ G(2d,2p) level of theory. The experimental and computational results reported allow to extend the discussion about the influence of the molecular structure on the dissociation enthalpy of the N-O bonds for quinoxaline 1,4-dioxide derivatives. As found previously, similar N-O bond lengths in quinoxaline-1,4-dioxide compounds are not linked with N-O bonds having the same strength.

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“…[14,15] Our group has vast experience in the synthesis and biological evaluation of multiple quinoxaline 1,4-di-Noxide derivatives, having identified a broad spectrum of anti-infective activities. [16][17][18][19][20][21][22][23][24][25][26] The evaluation of several libraries of compounds led us to find a series with high in vitro activity against T. cruzi. [27] This finding allowed us to establish structural features for maintaining high in vitro activity against the parasite (Scheme 1).…”

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confidence: 99%

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

Torres

Moreno‐Viguri

Galiano

et al. 2013

European Journal of Medicinal Chemistry

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ABSTRACT. As a continuation of our research and with the aim of obtaining new agents against Chagas disease, an extremely neglected disease which threatens 100 million people, eighteen new quinoxaline 1,4-di-N-oxide derivatives have been synthesized following the Beirut reaction. The synthesis of the new derivatives was optimized through the use of a new and more efficient microwave-assisted organic synthetic method. The new derivatives showed excellent in vitro biological activity against Trypanosoma cruzi. Compound 17, which was substituted with 2 fluoro groups at the 6-and 7-positions of the quinoxaline ring, was the most active and selective in the cytotoxicity assay. The electrochemical study showed that the most active compounds, which were substituted by electron-withdrawing groups, possessed a greater ease of reduction of the N-oxide groups.

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Synthesis and anticancer activity evaluation of new 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethyl-quinoxaline 1,4-di-N-oxide derivatives

Cited by 99 publications

References 10 publications

Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives

Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives

Energetic and structural characterization of 2‐R‐3‐methylquinoxaline‐1,4‐dioxides (R = benzoyl or tert‐butoxycarbonyl): experimental and computational studies

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

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