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

VALENSI · Vol. ume No. 2 (2022) · pp. 221–231

DOI
10.15408/jkv.v8i2.25279
ISSN
2548-3013, 2460-6065
Published
2022-11-25
Publisher
Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University
Language
eng

Abstract

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.

Keywords

Collaboration network of the authors

40 authors · 176 co-authorship links · showing the 40 most connected

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  • Syarif Hidayatullah State Islamic University Jakarta
  • Affiliation unknown
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  • Same organisation
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  • Thicker line = more joint articles · bigger circle = more articles
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Co-authorOrganisationJoint articles
Isalmi AzizAffiliation unknown11
Lukman MakmurAffiliation unknown8
Norio AimiAffiliation unknown7
Mariko KitajimaAffiliation unknown7
Hiromitsu TakayamaAffiliation unknown7
Euis Holisotan HakimAffiliation unknown7
Sjamsul Arifin AchmadAffiliation unknown6
Nanda SaridewiAffiliation unknown5
Adawiah AdawiahAffiliation unknown4
Agustino ZulysAffiliation unknown4
Lisa AdhaniAffiliation unknown4
Elvira HermawatiAffiliation unknown4
Lia Dewi JuliawatyAffiliation unknown3
Yana Maolana SyahAffiliation unknown3
Tarso RudianaAffiliation unknown3
Eri BachtiarAffiliation unknown2
Dede SukandarAffiliation unknown2
Latifah TulhusnaAffiliation unknown2
Robby RoswandaAffiliation unknown2
Ade DanovaAffiliation unknown2
Warinthorn ChavasiriAffiliation unknown2
Anita AlniAffiliation unknown2
Fera KurniadewiAffiliation unknown2
Sjamsul Arifin AchmadAffiliation unknown2
Rusjdi TaminAffiliation unknown2
Euis Holisotan HakimAffiliation unknown2
Badrul UlumAffiliation unknown2
Adid Adep DwiatmokoAffiliation unknown2
Anna MuawanahSyarif Hidayatullah State Islamic University Jakarta2
Yulyani Nur AzizahAffiliation unknown2
Selviana RustantiAffiliation unknown1
Uly Fitria BaleAffiliation unknown1
Rizka FadhillaAffiliation unknown1
Fitri Nur RamadhanAffiliation unknown1
Muhamad Abdulkadir MartoprawiroAffiliation unknown1
Suci Zulaikha HildayaniAffiliation unknown1
Alfhons Daniel SirampunAffiliation unknown1

Affiliations come from OpenAlex; journal OAI-PMH metadata carries none. Authors without an OpenAlex ID are matched by name, which can merge or split people.

Metadata source: OAI-PMH (metadata jurnal) http://journal.uinjkt.ac.id/index.php/valensi/oai, first harvested 10 Nov 2026, last seen 10 Nov 2026.
Original metadata (oai_dc) 
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	<dc:title xml:lang="en">Synthesis and Antibacterial Activity of 1,3,5,7-Tetrahydroxy-9,10-Anthraquinone and Anthrone Derivatives</dc:title>
	<dc:creator xml:lang="en">Nurbayti, Siti</dc:creator>
	<dc:creator xml:lang="en">Mujahidin, Didin</dc:creator>
	<dc:creator xml:lang="en">Syah, Yana Maolana</dc:creator>
	<dc:subject xml:lang="en">Anthraquinone</dc:subject>
	<dc:subject xml:lang="en">anthrone</dc:subject>
	<dc:subject xml:lang="en">antibacterial</dc:subject>
	<dc:subject xml:lang="en">methylation</dc:subject>
	<dc:subject xml:lang="en">reduction</dc:subject>
	<dc:description xml:lang="en">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.</dc:description>
	<dc:publisher xml:lang="en">Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University</dc:publisher>
	<dc:date>2022-11-25</dc:date>
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	<dc:identifier>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279</dc:identifier>
	<dc:identifier>10.15408/jkv.v8i2.25279</dc:identifier>
	<dc:source xml:lang="en">Jurnal Kimia Valensi; Jurnal Kimia VALENSI Volume 8, No. 2, November 2022; 221-231</dc:source>
	<dc:source>2548-3013</dc:source>
	<dc:source>2460-6065</dc:source>
	<dc:language>eng</dc:language>
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	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16997</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16998</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16999</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/17000</dc:relation>
	<dc:rights xml:lang="en">Copyright (c) 2022 Siti Nurbayti, Didin Mujahidin, Yana Maolana Syah</dc:rights>
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