Initial study on the synthesis of 1-(4'-isopropilbenzil)-1,10-phenanthrolinium bromide from cuminyl alcohol, a potent antimalarial

Because of the rapid development of malaria resistance to conventional drugs such as chloroquine, pamaquine, amodiakuin, meflokuin and pyrimethamin, the development of new and effective antimalarial drugs is highly desirable. In this work, an initial study on the synthesis of potent antimalarial, 1-(4’-isopropylbenzyl)-1,10-phenantrolinium bromide, from cuminyl alcohol has been carried out. The synthesis was performed through two stages of reaction. First, the synthesis of cuminyl bromide by bromination reaction and the second, the synthesis of 1-(4’-isopropylbenzyl)-1,10- phenanthrolinium bromide by bimolecular nucleophilic substitution reaction (SN2). Structural analyses of the bromination reaction of cuminyl alcohol and PBr3 using FTIR, 1H-NMR and GC-MS showed the formation yellowish liquid cuminyl bromide. Furthemore, the formed cuminyl bromide was reacted with 1,10-phenanthroline in acetone at 56 °C for 12 h to afford orange solid phenantrolinium salt target with melting point of 165-167 °C.