Tetrasubstituted pyrazinones derived from the reaction of praziquantel with N-bromosuccinimide

Qingjie Zhao; Chunkai Wang; Edward L Ezell; Yuxiang Dong; Jonathan L Vennerstrom

doi:10.1016/j.tetlet.2014.06.083

Tetrasubstituted pyrazinones derived from the reaction of praziquantel with N-bromosuccinimide

Tetrahedron Lett. 2014 Aug 6;55(32):4463-4465. doi: 10.1016/j.tetlet.2014.06.083.

Authors

Qingjie Zhao¹, Chunkai Wang¹, Edward L Ezell², Yuxiang Dong¹, Jonathan L Vennerstrom¹

Affiliations

¹ University of Nebraska Medical Center, College of Pharmacy, 986025 Nebraska Medical Center, Omaha, NE, United States.
² University of Nebraska Medical Center, Eppley Institute for Research in Cancer, 986105 Nebraska Medical Center, Omaha, NE, United States.

Abstract

When praziquantel was exposed to N-bromosuccinimide in the presence of ethanol, a tricyclic 3-bromo-1-ethoxy pyrazinone was formed. From this and the analogous 1,3-dibromopyrazinone, a small library of 3-alkylamino-1-ethoxy, 1,3-dialkoxy, 3-alkoxy-1-bromo, and 3-alkylamino-1-bromo substituted pyrazinones were synthesized in high yields.

Keywords: N-bromosuccinimide; piperazinone; praziquantel; pyrazinone.

Grants and funding

R21 AI076783/AI/NIAID NIH HHS/United States