Honors College Theses

Publication Date

5-11-2024

Major

Biochemistry (B.S.)

Document Type and Release Option

Thesis (restricted to Georgia Southern)

Faculty Mentor

Brandon Quillian

Abstract

In the wake of the preparation of chromenoquinoxalines, computational studies suggest this molecular platform could serve as a lead to develop drugs to treat ER+ breast cancers. Due to their poor solubility in aqueous environments, methods were developed to attach pendant groups to improve their solubility. A synthetic pathway in preparation of 6-phenyl-6-(2-(pyrrolidine-1-yl)ethoxy)-6H-chromeno[3,4-b]quinoxaline (4), was achieved. The first step of this pathway involves the reaction of 3-hydroxyflavone with copper (II) bromide in 2-chloroethanol to produce 2-(2-chloroethoxy)-3,3-dihydroxy-2-phenylchroman-4-one (1). Compound 1 reacts cleanly with o-phenylenediamine to yield 6-(2-chloroethoxy)-6-phenyl-6H-chromeno[3,4-b]quinoxaline (2), which reacts with pyrrolidine in the presence of NaI and a base at 90°C for 4-5 days providing the target molecule (4) in good to moderate yield. Compounds 1, 2, and 4 were characterized by 1H, 13C, and NMR, ESI-TOF High-resolution Mass spectrometry, and single-crystal X-ray crystallography. Interesting anecdotes on the reaction chemistry of this class of molecules and computational data on future leads in potential anti-cancer reagent development are provided.

Thesis Summary

In the wake of the preparation of chromenoquinoxalines, computational studies suggest this molecular platform could serve as a lead to develop drugs to treat ER+ breast cancers. Due to their poor solubility in aqueous environments, methods were developed to attach pendant groups to improve their solubility in preparation for in vitro studies. A synthetic pathway in preparation of 6-phenyl-6-(2-(pyrrolidine-1-yl)ethoxy)-6H-chromeno[3,4-b]quinoxaline was achieved. Synthesized compounds were characterized by 1H, 13C, and NMR, ESI-TOF High-resolution Mass

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