SYNTHESIS OF 2-HIDROXYXANTHONE FROM XANTHONE AS A BASIC MATERIAL FOR NEW ANTIMALARIAL DRUGS


Amanatie Amanatie, Jumina Jumina, Mustofa Mustofa, Hanafi M, La Ode Kadidae, Sahidin I

Abstract


Objective: The purpose of this research is to synthesize 2-hydroxyxanthone from xanthone and to evaluate its antiplasmodial activity.

Methods: The synthesis of 2-hydroxyxanthone followed the sequence of these synthetic stages, namely: 2-nitroxanthone, 2-aminoxanthone, and 2-hydroxyxanthone. The products were separated by chromatography methods including thin layer chromatography and vacuum liquid chromatography. Compound structures of the isolated products were determined based on their infrared and nuclear magnetic resonance spectra. To support these findings, the spectra were also matched to the corresponding data from literatures. The biological properties of the synthetic compound were evaluated toward Plasmodium falciparum 3D7.

Results: 2-nitroxanthone was obtained as a brownish-yellow crystal in 69.00% yield with Madhya Pradesh of 181°C. Reduction of 2-nitroxanthone using SnCl2.2H2O/hydrogen chloride produced 2-aminoxanthone as a pale-yellow solid in 60.60% yield. Finally, the desired 2-hydroxyxanthone was achieved by initially reacting 2-aminoxanthone with sodium nitride to produce diazonium salt. Then, hydrolysis of the salt yielded 2-hydroxyxanthone as a white solid in 69.81% yield. Synthesis of 2-hydroxyxanthone from xanthone had an overall yield of38.35%. In vitro antiplasmodial assay against P. falciparum 3D7 showed that the half maximal inhibitory concentration value was 0.44 μg/mL.

Conclusions: An antimalarial compound (2-hydroxyxanthone) was successfully synthesized from xanthone in three steps of synthetic reactions, i.e., the formation of 2-nitroxanthone, 2-aminoxanthone, and 2-hydroxyxanthone.

 


Keywords


2-nitroxanthone, 2-aminoxanthone, 2-hydroxyxanthone, in-vitro, antiplasmodium, Plasmodium falciparum 3D7.

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About this article

Title

SYNTHESIS OF 2-HIDROXYXANTHONE FROM XANTHONE AS A BASIC MATERIAL FOR NEW ANTIMALARIAL DRUGS

Topics

Organic Chemistry and pharmacology

Keywords

2-nitroxanthone, 2-aminoxanthone, 2-hydroxyxanthone, in-vitro, antiplasmodium, Plasmodium falciparum 3D7.

DOI

10.22159/ajpcr.2017.v10i12.19858

Date

01-12-2017

Additional Links

Manuscript Submission

Journal

Asian Journal of Pharmaceutical and Clinical Research
Vol 10 Issue 12 December 2017 Page: 242-246

Print ISSN

0974-2441

Online ISSN

2455-3891

Statistics

18 Views | 41 Downloads

Authors & Affiliations

Amanatie Amanatie
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Yogyakarta State University, Yogyakarta 55281, Indonesia.
Indonesia

Jumina Jumina
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Yogyakarta 55281, Indonesia.
Indonesia

Mustofa Mustofa
Department of Medicine, Faculty of Medicine, Gadjah Mada University, Yogyakarta 55281, Indonesia.
Indonesia

Hanafi M
Pusat Penelitian Kimia, Lembaga Ilmu Pengetahuan Indonesia, Serpong, Tanggerang 15314, Indonesia.
Indonesia

La Ode Kadidae
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Halu Oleo, Kampus Baru Anduonohu, Kendari, Sulawesi, Tenggara 93232, Indonesia
Indonesia

Sahidin I
Department of Pharmacy, Faculty of Pharmacy, Universitas Halu Oleo, Kampus Baru Anduonohu, Kendari, Sulawesi, Tenggara 93232, Indonesia.
Indonesia


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