Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction

In recent years, great efforts have been dedicated to the design of compounds acting as selective inhibitors of the HIV-1 reverse transcriptase (RT). Due to the promissory results previously attained with some quinoxaline derivatives, we aimed to improve the specific standard Hinsberg synthetic pathway by means of biocatalysis or microwave (MW) irradiation. Both techniques rendered the products in very good yields. However, employing the microwave-assisted organic synthesis (MAOS), in the absence of solvent, the same reactions may be completed in minutes. Some of these quinoxalinone derivatives exhibited good inhibitor activity against some human tumoral cells and the lymphoma related to HIV-1.

Graphical abstractSynthesis by Hinsberg reaction of quinaxolinone and benzoquinoxalinone derivatives under microwave irradiation, or employing biocatalysis, aiming at improving reaction times and yields of the standard reaction.Download full-size image