Title page for ETD etd-11102005-141121
|Type of Document
||Hubieki, Marina Patricia
||Toward the design, synthesis and evaluation of Protein Kinase C inhibitors
|Gandour, Richard D.
|Brewer, Karen J.
|Castagnoli, Neal Jr.
|Tanko, James M.
|Date of Defense
Protein Kinase C (PKC) represents an important regulatory element in the
signal transduction pathways of mammalian cells. Research interest has increased
enormously since the discovery that PKC plays critical roles in cell differentiation,
tumor promotion, oncogenesis and cell regulatory processes.
The primary driving force of this project was the study and development of
enantioselective PKC inhibitors. To accomplish this objective the four stereoisomers,
(2S/4S)-, (2RI4S)-, (2R14R)-, and (2S/4R)-6-N,N-dimethyl-2-methyl-2-oxo-l,3-dioxa-
4-pentadecyl-6-aza-2-phosphacyclooctane bromides (la-d) were synthesized and
Long-alkyl chain optically pure epoxides, the key intermediates for the
synthesis, were prepared from relatively inexpensive glyceraldehyde surrogates.
Several other intermediates exhibited other biological responses including
spermicidal, anti-HIV, mycobactericidal, and anti-cancer activities.
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