Title page for ETD etd-11102005-141121

Type of Document Dissertation
Author Hubieki, Marina Patricia
URN etd-11102005-141121
Title Toward the design, synthesis and evaluation of Protein Kinase C inhibitors
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Gandour, Richard D. Committee Chair
Brewer, Karen J. Committee Member
Castagnoli, Neal Jr. Committee Member
Hudlicky, Tomas Committee Member
Tanko, James M. Committee Member
  • regulatory elements
Date of Defense 1996-04-14
Availability restricted
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 evaluated.

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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