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

https://doi.org/10.22146/ijc.21698

Ruslin Hadanu(1*), Sabirin Mastjeh(2), Jumina Jumina(3), Mustofa Mustofa(4), Mahardika Agus Widjayanti(5), Eti Nurwening Sholikhah(6)

(1) Department of Chemistry, Pattimura University, Ambon, Indonesia
(2) Laboratorium of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.
(3) Laboratorium of Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.
(4) Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.
(5) Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.
(6) Medical Faculty, Universitas Gadjah Mada, Yogyakarta, Indonesia 55281.
(*) Corresponding Author

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.


Keywords


1,10-phenanthroline; (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide; 4 methoxybenzaldehyde; antiplasmodial activities

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References

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DOI: https://doi.org/10.22146/ijc.21698

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