ChemInform Abstract: New Quinoxaline 1,4‐Di‐N‐oxides: Anticancer and Hypoxia‐Selective Therapeutic Agents.

Abstract

New Quinoxaline 1,4-Di-N-oxides: Anticancer and Hypoxia-Selective Therapeutic Agents. -A series of novel quinoxaline 1,4-di-N-oxides is prepared and evaluated for antitumor and hypoxia-selective cytotoxic activities. Compound (VIb) is the most promising substance acting both as an antitumor and as a hypoxia-selective agent. Compounds (IIIb) and (Xd) are the most toxic against liver carcinoma (Hepg2). -(ISMAIL*, M. M. F.; AMIN, K. M.; NOAMAN, E.; SOLIMAN, D. H.; AMMAR, Y. A.; Eur.

Enzyme-Activated Generation of Reactive Oxygen Species from Heterocyclic N-Oxides under Aerobic and Anaerobic Conditions and Its Relevance to Hypoxia-Selective Prodrugs

“…179−181 Hypoxia-selectivity varies widely among these agents. 144,[173][174][175][176][177][178]182 Finally, some phenazine Noxides display properties similar to TPZ. 183 Redox-activated DNA cleaving activity has been described for phenazine Noxides including the natural product myxin (9).…”

Synthesis, Characterization and Biological Evaluation of Some Quinoxaline Derivatives: A Promising and Potent New Class of Antitumor and Antimicrobial Agents

“…The anticancer evaluation of the newly synthesized quinoxaline derivatives showed that among the tested compounds 8-bromo-4-chlorotetrazolo [1,5- (11) showed the best result, exhibiting the highest inhibitory effects towards the three tumor cell lines, which were higher than that of the reference doxorubicin and these compounds were non-cytotoxic on the normal cells (IC 50 values >100 µg/mL). In addition, compounds 4, 5a, 5b, 9 and 11-13 exhibited the highest degrees of inhibition against the strains of Gram positive and negative bacteria.…”

“…Accordingly, we need to design new compounds having anticancer and antimicrobial activity at the same time. Quinoxaline derivatives display a broad spectrum of biological activities including antimicrobial [5][6][7], antiviral [8], antiinflammatory [9,10], anticancer [11][12][13][14], antimalarial [15], antitubercular, antileishmanial and kinase inhibitors [16][17][18][19]. Some quinoxaline derivatives have a cytotoxic effect on human cancer cell lines [20] and they constitute useful intermediates in organic synthesis and medicinal chemistry [21][22][23][24].…”

Experimental and computational analysis (DFT method) of some quinoxalinones and benzoxazinones: spectroscopic investigation (FT-IR, FT-Raman, UV-Vis, NMR)

“…2 Such compounds are also known to be active against transplant tumors. 4 Also, quinoxaline-based compounds have the ability to inhibit the metal corrosion and they are used in electroluminescent materials. 5,6 Physicochemical properties of inhibitors (e.g., electron density, geometric factors, molecular volume, etc.,) determine their effectiveness of corrosion, while the process of adsorption depends on the type of metal, the nature of inhibitor, and the electrochemical potential at the metal-solution surface.…”

“…13,14 Bearing in mind the biological, structural, and industrial importance of quinoxaline-and benzoxazine-based compounds, we used these previously synthesized compounds for DFT calculations. 13 The studied quinoxaline and benzoxazine derivatives namely 3,4-dihydro-3-[2-oxo-2-(4-methoxyphenyl) ethylidene]-2(1H)-quinoxalinone (1), 3,4-dihydro-3-(5-methyl-2-oxo-hex-5-enylidene)-2(1H)-quinoxalinone (2), 3,4-dihydro-3-[2-oxo-2-(3-nitrophenyl)ethylidene] -2(1H)-quinoxalinone (3) and 3,4-dihydro-3-[2-oxo-2-(3-N-acetylphenyl)ethylidene]-1,4-benzoxazin-2-one (4) are presented in Figure 1. In this study, the equilibrium conformation of selected compounds was predicted theoretically using B3LYP/6-311?G(d,p) level of theory.…”