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Dissertation Information for John Jeffrey McAtee

NAME:
- John Jeffrey McAtee

DEGREE:
- Ph.D.

DISCIPLINE:
- Chemistry

SCHOOL:
- Emory University (USA) (1999)

ADVISORS:
- Dennis C. Liotta

COMMITTEE MEMBERS:
- Albert Padwa
- Frank E. McDonald

MPACT Status: Fully Complete

Title: Development and investigation of carboranyl nucleosides for boron neutron capture therapy of cancer and fluorinated nucleoside analogs as antiviral agents for the treatment of human immunodeficiency virus (HIV) and hepatitis B (HBV)

Abstract: "This dissertation examines the synthesis of an oxathiolane sugar--containing carboranyl nucleoside and the enzymatic resolution of the nucleoside racemate into the separate enantiomers. The separated enantiomers were tested individually for toxicity, cellular uptake and retention, and phosphorylation to gauge their effectiveness as potential agents for Boron Neutron Capture Therapy, a binary mode of cancer chemotherapy. Improvements in the existing synthetic procedures for obtaining oxathiolane nucleosides were developed and are presented in this dissertation.

This dissertation also details the investigation of fluorinated nucleoside analogs for use as antiviral agents against Human Immunodeficiency Virus (HIV) and Hepatitis B (HBV). The use of nucleosides as antiviral agents, particularly within the context of HIV and HBV, is examined. The role of fluorine in biomedicinal chemistry and synthetic methods for introducing fluorine into organic compounds is discussed. The synthesis of a potent non-toxic nucleoside, â-(D)-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-5-fluorocytidine (D4FC), is presented and efforts to improve its stability to acid are discussed. The development of a completely diastereoselective electrophilic fluorination of a chiral, non-carbohydrate sugar ring precursor and its application to the synthesis of and is presented in this several novel 2 ' -fluoronucleosides was also developed dissertation. Finally, the development of a diastereoselective synthesis and the biological evaluation of a novel 2 ' -fluorinated analog of D4FC is discussed. It was found that â-(D)-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-2 ' -fluoro-5-fluorocytidine (2 ' -Fluoro-D4FC) retained the good antiviral activity of D4FC with respect to HIV and HBV, but was significantly more acid stable."

MPACT Scores for John Jeffrey McAtee

A = 0
C = 0
A+C = 0
T = 0
G = 0
W = 0
TD = 0
TA = 0
calculated 2008-04-13 14:15:01

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