Synthesis of 5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone
Faculty Mentor
Dr. John DiCesare
Location
Russell Union Ballroom
Type of Research
On-going
Session Format
Poster Presentation
College
College of Science & Mathematics
Department
Chemistry
Abstract
5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone can be synthesized from 5,8-Dihydroxy-1,4-naphthoquinone (naphthazarin). Naphthazarin is a hydroxylated derivative of 1,4-naphthoquinone in which hydrogen atoms at the 5 and 8 positions are replaced with hydroxyl groups. Naphthazarin has demonstrated cytotoxic activity in cancer cell lines and is known to induce apoptosis through increased cytosolic Ca²⁺ levels. The objective of this study is to synthesize 5,8-dihydroxy-1,4-naphthoquinone as a key intermediate for the preparation of TU100 analogs. TU100 is a naphthoquinone adduct from a 3+2 cycloaddition reaction between N-methyl-4-hydroxyisoquinolinium iodide and 1,4-naphthoquinone, following the method established by DiCesare et al., and current research aims to synthesize 5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone as precursor compounds to react with N-methyl-4-hydroxyisoquinolinium Iodide. These compounds will be synthesized from naphthazarin to form new oxygenated TU100 analogs and to evaluate their biological potential.
Synthesis of naphthazarin is achieved via a double Friedel–Crafts acylation reaction between 1,4-dimethoxybenzene and maleic anhydride. The reaction product was isolated using vacuum filtration and extraction techniques, followed by recrystallization for purification. Product formation and purity were assessed using proton nuclear magnetic resonance (¹H NMR) spectroscopy. The hydroxyl groups on naphthazarin will be methylated and acetylated to form the title compounds and those compounds will be reacted with N-methyl-4-hydroxyisoquinolinium iodide to form TU100 analogs containing naphthazarin functionality.
Program Description
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Start Date
4-23-2026 10:00 AM
End Date
4-23-2026 12:00 PM
Recommended Citation
Michael, Darvika, "Synthesis of 5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone" (2026). GS4 Student Scholars Symposium. 86.
https://digitalcommons.georgiasouthern.edu/research_symposium/2026/2026/86
Synthesis of 5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone
Russell Union Ballroom
5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone can be synthesized from 5,8-Dihydroxy-1,4-naphthoquinone (naphthazarin). Naphthazarin is a hydroxylated derivative of 1,4-naphthoquinone in which hydrogen atoms at the 5 and 8 positions are replaced with hydroxyl groups. Naphthazarin has demonstrated cytotoxic activity in cancer cell lines and is known to induce apoptosis through increased cytosolic Ca²⁺ levels. The objective of this study is to synthesize 5,8-dihydroxy-1,4-naphthoquinone as a key intermediate for the preparation of TU100 analogs. TU100 is a naphthoquinone adduct from a 3+2 cycloaddition reaction between N-methyl-4-hydroxyisoquinolinium iodide and 1,4-naphthoquinone, following the method established by DiCesare et al., and current research aims to synthesize 5,8-Dimethoxy-1,4-naphthoquinone and 5,8-Diacetoxy-1,4-naphthoquinone as precursor compounds to react with N-methyl-4-hydroxyisoquinolinium Iodide. These compounds will be synthesized from naphthazarin to form new oxygenated TU100 analogs and to evaluate their biological potential.
Synthesis of naphthazarin is achieved via a double Friedel–Crafts acylation reaction between 1,4-dimethoxybenzene and maleic anhydride. The reaction product was isolated using vacuum filtration and extraction techniques, followed by recrystallization for purification. Product formation and purity were assessed using proton nuclear magnetic resonance (¹H NMR) spectroscopy. The hydroxyl groups on naphthazarin will be methylated and acetylated to form the title compounds and those compounds will be reacted with N-methyl-4-hydroxyisoquinolinium iodide to form TU100 analogs containing naphthazarin functionality.
