Synthesis and Antibacterial Activity of 1,3,5,7-Tetrahydroxy-9,10-Anthraquinone and Anthrone Derivatives

Siti Nurbayti (Department of Chemistry, Faculty of Science and Technology, UIN Syarif Hidayatullah Jakarta Jl. Ir. H. Juanda No. 95, Ciputat, South Tangerang 15412, Indonesia)
Didin Mujahidin (Department of Chemistry, Faculty of Mathematics and Natural Science, Bandung Institute of Technology Jl. Ganesha No. 10, Bandung, 40132, Indonesia)
Yana Maolana Syah (Department of Chemistry, Faculty of Mathematics and Natural Science, Bandung Institute of Technology Jl. Ganesha No. 10, Bandung, 40132, Indonesia)

VALENSI
Jurnal Kimia VALENSI Volume 8, No. 2, November 2022

In this research, the synthesis of 1,3,5,7-tetrahydroxy-9,10-anthraquinone (1) and two anthrone derivatives, 1,3,5,7-tetrahydroxy-10H-anthracene-9-one (2) and 1-hydroxy-3,5,7,9-tetramethoxyanthracene (3) has been done. Compound 1 was synthesized by a symmetrical condensation reaction of 3,5-dihydroxybenzoic acid in concentrated sulfuric acid. Reduction of the carbonyl group in compound 1 with SnCl2/HCl-HOAc affords compound 2. Compound 3 was prepared by modifying the hydroxy groups of compound 2 by a methylation reaction. The synthesized compounds were identified using nuclear magnetic resonance spectroscopy (NMR) and a high-resolution mass spectrometry (HR-ESI-MS). The antibacterial activity test of the synthesized compounds against four pathogenic bacteria, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi, was carried out using the microdilution method. Compound 3 showed moderate activity against B. subtilis, E. coli and S. typhi with a MIC value of 37.5 µg/mL. Moderate activity was also shown by compound 2 against S. aureus, while compound 1 showed weak activity with a MIC value of 75 µg/mL against the four test bacteria.