Date Approved

8-20-2019

Embargo Period

8-21-2019

Document Type

Thesis

Degree Name

M.S. Pharmaceutical Sciences

Department

Chemistry & Biochemistry

College

College of Science & Mathematics

Advisor

Jonnalagadda, Subash

Committee Member 1

Ramanujachary, Kandalam

Committee Member 2

Hoy, Erik

Keywords

metronidazole, Baylis-Hillman reaction

Subject(s)

Imidazoles; Drug development

Disciplines

Medicinal and Pharmaceutical Chemistry

Abstract

Imidazoles are heterocyclic small molecules that play a major role in medicinal chemistry and drug discovery. There are several drugs in the market which contain imidazoles as the pharmacophore. Metronidazole, an imidazole containing compound, is a prominent antibiotic and antiprotozoal medication used for the treatment of a variety of infections such as amoebiasis, trichomoniasis, bacterial vaginosis, etc. The current work involves the synthesis of small molecule libraries of imidazoles derived from metronidazole using Baylis-Hillman (BH) reaction. BH reaction is a carbon-carbon bond forming reaction and involves the coupling of aldehydes or imines with activated alkenes such as acrylates, acrolein, or vinyl ketones to produce functionalized allylic alcohols and amines. These products were further functionalized with metronidazole derived amines for potential use as therapeutic agents.

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