Date of Award
2018
Document Type
Thesis
Degree Name
Bachelors
Department
Natural Sciences
First Advisor
Scudder, Paul
Area of Concentration
Natural Sciences
Abstract
Over the past few decades there have been very few breakthrough discoveries in the field of antibiotics. Designing an effective drug is not a simple task, and requires a long and grueling selection and optimization process. The analogue approach is a very effective method in drug design and was applied to the N-aryl-oxazolidinone moiety in an effort to explore the structure activity relationship among this series. Dr. Tucker proposed a heterocyclic aromatic species as a substituent for placement at the N-aryl site of the oxazolidinone moiety. Specifically, we hoped to replace the N-phenyl “B-ring” in the active linezolid oxazolidinone core moiety with a 5-subsituted-1,3,4-oxadiazole. The synthesis of N-(5-phenyl-1,3,4-oxadiazole)-oxazolidin-2-one was attempted. With 2-amino-5-phenyl- 1,3,4-oxadiazole exhibiting antibacterial properties on its own, this moiety became the lead heterocyclic aromatic substituent. With the ever-increasing rates of antibiotics resistance, developing and implementing novel antibiotic moieties is necessary for the survival of our species. There is a very real possibility that in our lifetime, we may face a “post antibiotic era,” and developing syntheses for these analogues represents a small part of a much larger ambition.
Recommended Citation
Bruch, David J., "NOVEL ANTIBIOTIC DESIGN: SYNTHESIS AND OPTIMIZATION OF N-HETEROCYCLIC OXAZOLIDINONES" (2018). Theses & ETDs. 5486.
https://digitalcommons.ncf.edu/theses_etds/5486