University of Memphis HomepageChemistry Homepage

 

  


Peter K. Bridson, Associate Professor and Chair

lab

Synthesis of Heterocyclic Compounds

Bio-Organic and Medicinal Chemistry

  • Adenosine receptor ligands

Publications

 
Purine Analogs and Derivatives:
Two purines, adenine and guanine, are components of the nucleic acids, DNA and RNA. Their nucleosides and nucleotides also have many significant roles in metabolism and its regulation. Other naturally occurring purines are precursors or derivatives of adenine and guanine, or alkaloids like theophylline and caffeine.

 purines

Many pharmaceuticals, particularly anticancer and antiviral drugs, are structurally related to naturally occurring purines or their nucleosides. Examples include allopurinol, acyclovir, and pentostatin. These and related compounds selectively affect biological processes by interacting with enzymes or receptors in place of the natural ligands that they resemble.

drugs

Research in my group involves the design and synthesis of derivatives and analogs of the naturally occurring purines and their nucleosides. Most of our products are submitted to other research groups for pharmacological screening. Examples of recently prepared compounds are shown below.

analogs
Publications:
  1. P. K. Bridson, W. Markiewicz, and C. B. Reese; Conversion of Guanosine into its N2‑Methyl Derivative, Journal of the Chemical Society, Chemical Communications 1977, 447-448.
  2. P. K. Bridson, W. Markiewicz, and C. B. Reese; Acylation of 2',3',5'-Tri-O-acetylguanosine, Journal of the Chemical Society, Chemical Communications 1977, 791-792.
  3. S. Neidle, A. Achari, G. M. Sheldrick, C. B. Reese, and P. K. Bridson; The Crystal and Molecular Structure of 2',3',5'-Tri-O-acetyl-6-O-(mesitylenesulfonyl)guanosine, Acta Crystallographica 1978, B34, 2794-2798.
  4. P. K. Bridson and C. B. Reese; The Conversion of Guanosine into its 2-N-Methyl and 2-N, 2-N-Dimethyl Derivatives, Bioorganic Chemistry 1979, 8, 339-349.
  5. P. K. Bridson, J. Jiricny, O. Kemal, and C. B. Reese; Reactions Between Ribonucleoside Derivatives and Formaldehyde in Ethanol Solution, Journal of the Chemical Society, Chemical Communications 1980, 208-209.
  6. R. Lohrmann, P. K. Bridson, and L. E. Orgel; Efficient Metal-Ion Catalyzed Template-Directed Oligonucleotide Synthesis, Science 1980, 208, 1464-1465.
  7. P. K. Bridson and L. E. Orgel; Catalysis of Accurate Poly(C)-Directed Synthesis of 3'-5'-Linked Oligoguanylates by Zn2+, Journal of Molecular Biology 1980, 144, 567-577.
  8. P. K. Bridson, H. Fakhrai, R. Lohrmann, L. E. Orgel, and M. Van Roode; Template-Directed Synthesis of Oligoguanylic Acids - Metal-Ion Catalysis, Origins of Life 1981, 3, 233-239.
  9. R. Lohrmann, P. K. Bridson, and L. E. Orgel; Condensation of Activated Diguanylates on a Poly(C) Template, Journal of Molecular Evolution 1981, 17, 303-306.
  10. P. K. Bridson and A. R. Larrabee; Column Chromatography, Chapter 11 in “Laboratory Medicine”, Vol. 1, G. J. Race, ed. Harper and Row, Philadelphia, 1983.
  11. P. K. Bridson, R. A. Davis, and L. S. Renner; The Reaction of 5-Aminoimidazole-4-carboxamide with Orthoesters, Journal of Heterocyclic Chemistry 1985, 22, 753-755.
  12. P. K. Bridson, A. McGowan, C. M. Wilson, and F. Yeh; Intramolecular Cyclization of Ethyl w-(5-Amino-4-carbonylimidazol-1-yl)carboxylates, Journal of Heterocyclic Chemistry 1987, 24, 1155-1156.
  13. P. K. Bridson and T. P. Weirich; Cyclic Homologs of Xanthines I. Imidazo[4,5-e] [1,4]diazepine-5,8-diones, Journal of Heterocyclic Chemistry 1988, 25, 1179-1182.
  14. P. K. Bridson, H. A. Kurtz, and F. Sayyarpour; An NMR and Computational Study of Diazepinediones, Journal of Molecular Structure (THEOCHEM) 1989, 199, 175-181.
  15. P. K. Bridson and S. J. Lambert; Imidazo[4,5-e][1,3]diazepine-4,6-dione, A Novel Xanthine Analog, Journal of the Chemical Society, Perkin I 1990, 173-175.
  16. J. W. Daly, I. Hide, and P. K. Bridson; Imidazodiazepinediones: A New Class of Adenosine Receptor Antagonist, Journal of Medicinal Chemistry 1990, 33, 2818-2821.
  17. P. K. Bridson, G. Richmond, and F. Yeh; Preparation of Xanthine-3-acetic Acid and Some Derivatives, Synthetic Communications 1990, 20, 2459-2467.
  18. P. K. Bridson and R. E. Harry O'Kuru; 1-(5-Amino-1-b-D-ribofuranosylimidazol-4-carbonyl)-3,5-dimethylpyrazole, A New Intermediate for the Preparation of AICAR Analogs, Nucleosides and Nucleotides 1991, 10, 355-359.
  19. R. V. Lloyd, D. R. Duling, R. P. Mason, and P. K. Bridson; Microsomal Reduction of 3-Amino-1,2,4-benzotriazine-1,4-dioxide, Molecular Pharmacology 1991, 40, 440-445.
  20. P. K. Bridson; Synthesis of Deoxyazepinomycin, Heterocycles 1994, 38, 1007-1014.
  21. P. K. Bridson and R. V. Iyengar; Alkylation of 5-Cyanoimidazole-4-carboxamide, Heterocycles 1995, 41, 1271-1274.
  22. P. K. Bridson and X. Wang; Synthesis of 1-Substituted Xanthines, Synthesis 1995, 855-858.
  23. S. M. Ali and P. K. Bridson; Synthesis of Extended Carbamate and Urea Linked Thymidine Dimers, Nucleosides and Nucleotides 1996, 15, 1531-1543.
  24. P. K. Bridson, H. Huang, and X. Lin; 6-Amino-1,8-dihydro[4,5-e][1,3]diazepin-4(5H)-one, A Ring Expanded Analog of Guanine, Journal of the Chemical Society, Perkin I, 1996, 2257-2260.
  25. P. K. Bridson, X. Lin, N. Melman, X. Ji, and K. A. Jacobson, Synthesis and Adenosine Receptor Affinity of 7-b-D-ribofuranosylxanthine, Nucleosides and Nucleotides 1998, 17, 759-768.
  26. F. Giorgianni, P. K. Bridson, B. P. Sorrentino, J. Pohl, and R. L. Blakley, Inactivation of Aldophosphamide by Human Aldehyde Dehydrogenase Isozyme 3, Biochemical Pharmacology, 2000, 60, 325-338.
[U of M Homepage] [Chemistry Homepage] [Bridson Homepage]