Document Type
Dissertation/Thesis
Date Created
12-11-2020
Embargo Date
12-11-2022
Abstract
Anilinoacridines are a class of compounds that are known to intercalate DNA. This class of compounds can be used as a target therapy to combat cell growth and replication. The anilinoacridines, DNA, and topoisomerase II will form a ternary complex that results in numerous strand scissions leading to apoptosis. Previous research has shown that the anilinoacridines can have a short half-life and produce harmful side products as a result of hydrolysis. The half-life could increase if this structure was slightly altered by making a molecule that does not readily hydrolyze. N-(9’-Acridinyl)-O-phenylhydroxylamines can be synthesized in three steps starting with commercially available aryl bromides and a protected hydroxylamine using catalytic palladium. This organometallic reaction gives a simple way to prepare an O-substituted hydroxylamine. After hydrolysis, the resulting product can then be coupled to 9-chloroacridine to form the target molecules. Spectroscopy, such as 1H NMR, 13C NMR, COSY, and HSQC were used to determine the structure and purity of each synthesized product. The title compounds were then analyzed and evaluated for their binding to DNA using viscosity. Unfortunately, due to the difficulty of purification of the title compounds, viscosity measurements were attempted but lead to inconclusive results.
Keywords
organic chemistry, synthesis
Recommended Citation
Forster, Jana, "Synthesis and Evaluation of N-(9'-Acridinyl)-O-phenylhydroxylamines" (2020). Master's Theses. 192.
https://digscholarship.unco.edu/theses/192