Indonesian Journal of Chemistry
Vol 7, No 2 (2007)

SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE

Ruslin Hadanu (Department of Chemistry, Pattimura University, Ambon, Indonesia)
Sabirin Mastjeh (Laboratorium of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.)
Jumina Jumina (Laboratorium of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.)
Mustofa Mustofa (Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.)
Mahardika Agus Widjayanti (Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.)
Eti Nurwening Sholikhah (Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.)



Article Info

Publish Date
20 Jun 2010

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 55 oC. 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.

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Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...