Awesome and Easy Science Experiments about 5-Nitroquinoxaline

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Synthesis of 2-arylindole derivatives and evaluation as nitric oxide synthase and NFkappaB inhibitors

Development of small molecule drug-like inhibitors blocking both nitric oxide synthase and NFkappaB could offer a synergistic therapeutic approach in the prevention and treatment of inflammation and cancer. During the course of evaluating the biological potential of a commercial compound library, 2-phenylindole (1) displayed inhibitory activity against nitrite production and NFkappaB with IC50 values of 38.1 ¡À 1.8 and 25.4 ¡À 2.1 muM, respectively. Based on this lead, synthesis and systematic optimization have been undertaken in an effort to find novel and more potent nitric oxide synthase and NFkappaB inhibitors with antiinflammatory and cancer preventive potential. First, chemical derivatizations of 1 and 2-phenylindole-3-carboxaldehyde (4) were performed to generate a panel of N-alkylated indoles and 3-oxime derivatives 2-7. Second, a series of diversified 2-arylindole derivatives (10) were synthesized from an array of substituted 2-iodoanilines (8) and terminal alkynes (9) by applying a one-pot palladium catalyzed Sonogashira-type alkynylation and base-assisted cycloaddition. Subsequent biological evaluations revealed 3-carboxaldehyde oxime and cyano substituted 2-phenylindoles 5 and 7 exhibited the strongest nitrite inhibitory activities (IC50 = 4.4 ¡À 0.5 and 4.8 ¡À 0.4 muM, respectively); as well as NFkappaB inhibition (IC50 = 6.9 ¡À 0.8 and 8.5 ¡À 2.0 muM, respectively). In addition, the 6?-MeO-naphthalen-2?-yl indole derivative 10at displayed excellent inhibitory activity against NFkappaB with an IC50 value of 0.6 ¡À 0.2 muM.

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Reference£º
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N930 | ChemSpider