New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides

Amin, Kamelia M.; Ismail, Magda M. F.; Noaman, Eman; Soliman, Dalia H.; Ammar, Yousry A.

doi:10.1016/j.bmc.2006.06.038

Cited by 74 publications

(35 citation statements)

References 19 publications

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“…Quinoxaline 1,4-di-N-oxide derivatives even improve the biological results shown by their reduced analogues and are endowed with antiviral, anticancer, antibacterial and antiprotozoal activities. [5][6][7][8][9] There are many publications regarding 1,4-di-N-oxide derivatives, and more specifically alkyl and arylcarboxamide derivatives, in which their antibacterial and antimicrobial activities [10][11][12][13][14] have been reported or their capability to act as antitumoral agents [15,16] has been clearly demonstrated, thereby reflecting the growing interest in these structures over the past forty years.…”

Section: Tuberculosis (Mtbc) the Report Published By Who In 2009 Esmentioning

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: Tuberculosis (Mtbc) the Report Published By Who In 2009 Esmentioning

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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“…In the last two decades, they have been synthesized and evaluated with the objective of determining the influence of different substituents in positions 2 and 3 of the quinoxaline ring on their biological activity. [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.…”

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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“…The 6-chloro-2-(4-chlorophenyl)quinoxaline 1,4-dioxide 85 was potent cytotoxin with IC 50 of 0.9 µg/mL and potency of 75 µg/mL [97]. It was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2- [97].…”

Section: Anticancer Activitymentioning

confidence: 93%

“…Medicinally used anticancer drugs are mainly systemic anti-proliferative cytotoxins that preferentially kill rapidly dividing cells [97]. The 6-chloro-2-(4-chlorophenyl)quinoxaline 1,4-dioxide 85 was potent cytotoxin with IC 50 of 0.9 µg/mL and potency of 75 µg/mL [97].…”

Section: Anticancer Activitymentioning

confidence: 99%

Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

Ajani

2014

European Journal of Medicinal Chemistry

100

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New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides

Cited by 74 publications

References 19 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

Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

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