SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF(1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE
ABSTRACT: Synthesis of
(1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide from 1,10-phenanthroline
monohydrate and 4-methoxybenzaldehyde as starting material and evaluation of
its antiplasmodial activities have been carried out. The 4-methoxybenzyl
alcohol was prepared from 4-methoxy-benzaldehyde using sodium borohydride
(NaBH4) reagent and ethanol absolute solution. The mixture was refluxed for 3
h. To yield colorless dilution compound with 90.41 % in efficiency.
Furthermore, bromination of
4-methoxybenzyl alcohol with phosphorus bromide (PBr3) was conducted by
refluxing for 3 h. The product of this reaction was yellow liquid of
4-methoxybenzyl bromide, 79.03% yield and 95.34 % purity. The final step of
reaction was benzylation of 1,10-phenanthroline monohydrate with
4-methoxybenzyl bromide reagent. It was conducted by refluxing in aceton for 8
h at 55oC. The yield of the reaction was
(1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide (77.63%). It is pink solid
form, and its melting point is 192-193 oC. Identification of the product was
carried out by means of GC-MS, IR and 1H-NMR spectrometers. The in vitro
antiplasmodial activity on chloroquine-resistant Plasmodium falciparum FCR-3
strain and chloroquine sensitive P. falciparum D10 strain for (1)-N-(4-methoxybenzyl)-1,10-phenanthroline
bromide were determined by microscopic method. The result showed that after 72
h incubation, it has IC50 0.93±0.02 µM and 1.21±0.09 µM, respectively.
Keywords: 1,10-phenanthroline, (1)-N-(4-methoxybenzyl)-1,10-phenanthroline
bromide, 4 methoxybenzaldehyde, antiplasmodial activities
Author: Ruslin Hadanu, Sabirin
Mastjeh, Jumina, Mustofa, Mahardika Agus
Widjayant and Eti Nurwening Sholikhah
Journal Code: jpkimiagg070019
