A novel and easy two-step,microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity |
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| Authors: | Stella Manta Dimitra-Niki Gkaragkouni Eleni Kaffesaki Petros Gkizis Dimitra Hadjipavlou-Litina Eleni Pontiki Jan Balzarini Wim Dehaen Dimitri Komiotis |
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| Institution: | 1. Department of Biochemistry and Biotechnology, Laboratory of Bio-Organic Chemistry, University of Thessaly, 26 Ploutonos Str., 41221 Larissa, Greece;2. Department of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece;3. Aristotle University of Thessaloniki, Department of Pharmaceutical Chemistry, School of Pharmacy, 54124 Thessaloniki, Greece;4. Rega Institute for Medical Research, KU Leuven, 3000 Leuven, Belgium;5. Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium |
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| Abstract: | A novel, two-step, facile route for the synthesis of pyrrolo2,3-b]quinoxalines via 2,3-dioxopyrroles, enhanced by microwave irradiation, is presented. The newly synthesized 2,3-dioxo-5-halophenyl pyrrolo precursors 4a–c as well as the non-aromatized ethyl 2-(4-halophenyl)-1-methyl-2,4-dihydro-1H-pyrrolo2,3-b]quinoxaline-3-carboxylates 6a–c and the aromatized ethyl 2-(4-halophenyl)-1-methyl-1H-pyrrolo2,3-b]quinoxaline-3-carboxylates 7a–c were evaluated for their antioxidant, cytostatic, and antiviral properties. Most of them proved to be potent hydroxyl radical scavengers and inhibited in vitro lipid peroxidation. The compounds showed moderate antiproliferative activity, while 6a inhibited vaccinia virus at an EC50 value of 2 μM, and 4c and 6c inhibited Sindbis virus at EC50 values of 4 μM. |
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| Keywords: | Pyrroloquinoxaline Pyrrolidine Multicomponent reaction Antioxidant activity Antiviral activity Cytostatic activity |
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