The research activities in my laboratory are in the areas of bioorganic chemistry and organic synthesis. The overall theme of our research is the development of new synthetic strategies and methodologies that have general utility in the synthesis of steroid molecules possessing significant and potentially useful biological activity. We are particularly interested in the mechanism of steroid action and the molecular basis of drug design. We utilize biochemical and structural methods in addition to our efforts in the partial and total synthesis of biologically significant steroids.
A current area of interest involves studies related to the synthesis and biological evaluation of steroids containing nitrogen (azasteriods) and sulfur (thiosteroids). In the past these types of steroid structures have had an excellent history as inhibitors of enzymes required for steroid biosynthesis and thus growth and reproduction of a variety of pathogenic microorganisms. In this effort we are focusing on the chemical synthesis of new aza- and thiosteroids as potential antimicrobial agents.
Additional chemical studies are directed towards the remote functionalization of steroid side chains. The direct one-step functionalization of steroids at remote positions represents the future direction of steroid synthesis by eliminating many intermediate steps in the overall reaction scheme. We have developed several reagents for this purpose and continue to explore new reagents for use in this area.
Other related studies include the development of new reagents and extending the scope and utility of existing reagents currently in use in synthetic organic chemistry. These efforts are directed toward the synthesis of new steroidal products and developing improved syntheses of known steroids of biological interest.
Li, Y.; Wu, X.; Lee, T. B.; Isbell, E. K.; Parish, E. J.; Gorden, A. E. V. “An Effective Method for Allylic Oxidation of 5-en-Steroids Using tert-Butyl Hydroperoxide” J. Org. Chem., 2010, 75, 1807-1810.
Gandikota, J. S.; Sun, H.; Lu, D.; Neely, W. C.; Parish, E. J. “New Developments in the Synthesis of Steroidal 4, 6- Diem- 3- ones” in Current Topics in Steroid Research, Transworld Research Network, 2008, 6, 135-141.
Parish, E. J.; Luo, C.; Webb, T.; Gorden, J. D. “Synthesis of Ring C Oxysterols: Inhibitors of Sterol Biosynthesis” Lipids, 2007, 42, 35-40.
Gandikota, J. S.; Li, S.; Neely, C. W.; Parish, E. J. “Steroids with the Ability of Inhibit Aromatase in the Biosynthesis of Estrogen” in Current Topics in Medicinal Chemistry, Transworld Research Network, 2006, 4, 65-72.