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Home > Academics > College of Liberal Arts, Education, & Sciences > Science Programs > Chemistry, Biochemistry, & Physics > Faculty & Staff > Bruce S. Burnham
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Bruce S. Burnham

Associate Professor of Chemistry

Ph.D., University of North Carolina, Chapel Hill
Biochemistry, Medicinal, Organic and General Chemistry

Our group concentrates on the synthesis and subsequent testing of biologically active compounds. This includes the organic synthesis of new compounds and their characterization as well as the evaluation of their activities in biochemical screens.

The broad areas of investigation in our group are on anti-cancer, lipid-lowering and anti-inflammatory agents.

The types of compounds we are currently working on synthesizing are pyrrole nucleosides (see figure 1). The pyrrole nucleosides may behave as inhibitors of DNA synthesis, and thus cell replication given their structural similarities to parts of DNA. The synthesis of the compounds involves first the synthesis of a di- or tri-substituted pyrrole employing iminium intermediates starting from a simple phenylacetic acid or acetophenone. Then, a protected ribose is attached to the pyrrole ring via electrophilic (C-nucleosides) or nucleophilic (N-nucleosides) conditions.

Strucures of a Pyrrole C5-Nucleoside and a Pyrrole N-Nucleoside.

Publications (Bold indicates student author)

  • Holub, J.M.; Smith, D.C.; Evans, M.A.; Rifat, S.; Argenti, A.; Dalglish, G.A.; Wilson, D.L.; Taylor, B.M.; Berkowitz, J.D.; Krumpe, K.; Gupton, J.T.; Burnham, B.S. "Synthesis and Cytotoxicity of Substituted Ethyl 2-phenacyl-3-phenylpyrrole-4-carboxylates." Arch. Pharm. Pharm. Med. Chem. 2002 (In Preparation)
  • Burnham, B.S. "The Synthesis and Pharmacological Activity of Amine-Boranes." Current Medicinal Chemistry 2002 (In Preparation).
  • Evans, M.A.; Smith, D.C.; Holub, J.M.; Argenti, A.; Hoff, M.; Dalglish, G.A.; Wilson, D.L.; Taylor, B.M.; Berkowitz, J.D.; Burnham, B.S.; Krumpe, K.; Gupton, J.T.; Scarlett, T.C.; Durham, R.; Hall, I.H. "Synthesis and Cytotoxicity of Substituted Ethyl 2-phenacyl-3-phenylpyrrole-4-carboxylates." Arch. Pharm. Pharm. Med. Chem. 2002 (In Press)
  • Scarlett, T.C.; Durham, R.; Hall, I.H.; Crosswicks, R.J.; Berkowitz, J.D.; Burnham, B.S. "Synthesis and Cytotoxicity of Cyanoborane Adducts of N6-Benzoyladenine and 6-Triphenylphosphonylpurine." Metal Based Drugs 2002 (Submitted)
  • Gupton, J.T.; Burnham, B.S.; Krumpe, K.E.; Du, K.; Sikorsji, J.A.; Warren, A.E.; Barnes, C.; Hall, I.H. "Synthesis and Cytotoxicity of 2,4-Disubstituted and 2,3,4-Trisubstituted Brominated Pyrroles in Murine and Human Cultured Tumor Cells." Arch. Pharm. Pharm. Med. Chem. 2000, 333, 3-9.
  • Gupton, J.T.; Krumpe, K.E.; Burnham, B.S.; Webb, T.; Shuford, R.J.; Sikorski, J. "The Application of Vinylogous Imminium Salt Derivatives to a Regiocontrolled and Efficient Relay Synthesis of Lukianol A and Related Marine Natural Products." Tetrahedron 1999, 55, 14515-14522.
  • Gupton, J.T.; Burnham, B.S.; Byrd, B.D.; Krumpe, K.E.; Stokes, C.; Shuford, J.; Winkle, S.; Webb, T.; Warren, A.E.; Barnes, C.; Henry, J.; Hall, I.H. "The Cytotoxicity and Mode of Action of 2,3,4-Trisubstituted Pyrroles and Related Derivatives in Human Tmolt4 Leukemia Cells." Pharmazie 1999, 54, 691-697.
  • Burnham, B.S.; Gupton, J.T.; Krumpe, K.E.; Webb, T.; Shuford, J.; Bowers, B.; Warren, A.E.; Barnes, C.; Hall, I.H. "Cytotoxicity of Substituted Alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2-carboxylates in L1210 Lymphoid Leukemia Cells." Arch. Pharm. Pharm. Med. Chem. 1998, 331, 337-341.
  • Gupton, J.T.; Krumpe, K.E.; Burnham, B.S.; Dwornik, K.A.; Petrich, S.A.; Du, X.K.; Bruce, M.A.; Vu, P.; Vargas, M.; Keertikar, K.M.; Hosein, K.N.; Jones, C.R.; Sikorski, J.A. "The Application of Disubstituted Vinylogous Iminium Salts and Related Synthons to the Regiocontrolled Preparation of Unsymmetrical 2,3,4-Trisubstituted Pyrroles." Tetrahedron 1998, 45, 5075-5088.

Student Posters at Regional/National Meetings

  • Berkowitz, J.D.; Argenti, A.; Crosswicks, R.J.; Evans, M.A.; Burnham, B.S. "Synthesis of Pyrrole C- and N-Nucleosides as Inhibitors of IMP Dehydrogenase." Mid-Atlantic Regional Meeting of the Am. Chemical Soc., George Mason University, Fairfax, Virginia, May 28, 2002.
  • Berkowitz, J.D.; Crosswicks, R.J.; Evans, M.A.; Burnham, B.S. "Synthesis of Pyrrole C-Nucleosides as Inhibitors of IMP Dehydrogenase." Mid-Atlantic Regional Meeting of the Am. Chemical Soc., Towson University, Towson, Maryland, May 31, 2001.
  • Burnham, B.; Krumpe, K.; Gupton, J.; Byrd, B.; Peaty, N.; Winkel, S.; Shuford, J.; Warren, A.; Barnes, C.; Henry, J.; Hall, I. "Recent Developments Concerning The Antineoplastic Activity and Mode of Action of Pyrrole Derivatives Related to Marine Natural Products." SERMACS'98. Research Triangle Park, NC, November 1998.
  • Krumpe, K.; Gupton, J.; Burnham, B.; Holt, H.; Byrd, B.; Winkel, S.; Shuford, J.; Webb, T.; Harrison, A.; Boucher, M.; Hines, I.; Waters, P.; Wright, E.; Peaty, N.; Sikorski, J. "Progress on the Use of Vinylogous Iminium Salt Based Approached as Applied to the Synthesis of Pyrroles Containing Marine Natural Products." SERMACS'98. Research Triangle Park, NC, November 1998.

Project SEED Posters at Regional/National Meetings

  • 224th ACS National Meeting in Boston, MA, August 19, 2003. Presented a poster with SEED students Kam S. Lam and Sarah Glersaye and Rider students Kush Patel and Saltanat Najmi. "The Synthesis of Pyrrole C-Nucleosides as Anti-Cancer Agents."
  • 220th ACS National Meeting in Washington, DC, August 21, 2000. Presented a poster with SEED students Mafoloe Hoff and Rajmeet Mann and Rider student Richard Crosswicks, "Synthesis of Di- and Trisubstituted Pyrroles and Pyrrole Nucleosides as Anticancer and Hypolipidemic Agents."