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

Abstract

A novel, two-step, facile route for the synthesis of pyrrolo[2,3-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-pyrrolo[2,3-b]quinoxaline-3-carboxylates 6a-c and the aromatized ethyl 2-(4-halopheny1)-1-methyl-1H-pyrrolo[2,3-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 [mu M, and 4c and 6c inhibited Sindbis virus at EC50 values of 4 mu M. (C) 2014 Elsevier Ltd. All rights reserved.