Date of Award

Spring 2017

Thesis Type

Open Access

Degree Name

Honors Bachelor of Arts

Department

Chemistry

Sponsor

Dr. James D. Patrone

Committee Member

Dr. Kassandra J. Riley

Committee Member

Dr. Laurel Goj Habgood

Abstract

The field of medicinal chemistry requires efficient, novel drug development processes to sustain and advance the landscape of current pharmaceutical agents. To this end, fragment-based drug discovery (FBDD) is a methodology that aims to provide a balanced approach to the hit detection and lead optimization stage in the identification of small molecule agents (fragments). These small, low-molecular weight (mw<300 amu) molecules are employed in various biochemical assays to identify leads against a biological target. One challenge in FBDD is the synthesis of novel fragments containing heterocycles with a selective synthetic handle, a functional group designed to allow further modification. Heterocyclic fragments that allow for straightforward synthesis and modification are underrepresented in fragment libraries and offer the intriguing opportunity for rapid diversification into a fragment library from single, heterocyclic parent fragment. The imidazole is a heterocycle that presents a unique synthetic challenge for organic chemists, as current imidazole syntheses do not allow for regioselective synthesis of a 1,2,4-substitued imidazole. The research herein describes the approaches taken towards the challenge of synthesizing the 1,2,4-substituted imidazole parent fragment containing a hydrophilic moiety, synthetic handle, and phenyl ring derivative.

Rights Holder

Tyler Lafferty

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