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School of Chemical Sciences

Chemical Sciences

Peter Kenny

Peter Kenny Peter Kenny
B.Sc., M.Sc., Ph.D. (UCD) F.I.C.I
Lecturer, Organic Chemistry



Name: Dr Peter Kenny
Phone Number: 5689
Room Number: X120
Email Address:

 

Synthesis and Structural Characterisation of Biologically Active Compounds and Anion Sensing Agents

Synthesis of resveratrol analogues:

Resveratrol, 3, 4’, 5-trihydroxy-trans-stilbene, which is found in grapes, is a naturally occurring phytoalexin formed in response to fungal infections. It exhibits various biological properties including antifungal, antibacterial, anticancer, estrogenic and heart protecting activities. The preparation of analogues of resveratrol can be accomplished in good yields using the decarbonylative Heck reaction. The compounds are then tested for biological activity in a wide range of biological assays including breast, lung and central nervous system cancer cell lines.

Synthesis of dipeptide derivatives as cathepsin protease inhibitors:

Cathepsins are a complex group of cysteine proteases implicated in diseases such as rheumatoid arthritis, cancer and malaria. A potent cathepsin protease inhibitor based on the N-benzoyl-L-leucine glycine nitrile scaffold was previously prepared by this group. Current interest is the preparation of fluorinated analogues of the most potent inhibitors.

Synthesis of novel N-ferrocenoyl/ferrocenyl peptide derivatives:

The aim of this research proposal is the design and synthesis of novel N-ferrocenoyl/ferrocenyl peptide derivatives and investigations into their use as electrochemical sensory agents for anions and biological activity studies. Anions are known to play many ubiquitous roles in biological and chemical processes. We have prepared a series of novel N-ferrocene peptide derivatives containing amide NH groups that can co-ordinate and electrochemically recognize a variety of anionic guest species. Further research will involve the preparation of 1,1’-ferrocenoyl amino acids and peptide derivatives. These compounds should form orderly arrangements through hydrogen bonding. This should aid in the recognition of anions with selectivity as the binding site can be adjusted through choice of amino acids employed in the synthesis.

Recent Publications

  1. Semi-rigid N-para-Ferrocenyl(benzoyl)amino acid esters for biomaterials: synthesis and characterization of Fc-C6H4CONHCH(R)CO2Me where Fc = (?5 C5H5)Fe(?5 C5H4) and R = H, CH3, CH2CH(CH3)2, CH2C6H5 and the X-ray crystal structures of Fc-C6H4CO2Me and the L-alanine derivative Fc-C6H4CONHCH(CH3)CO2Me. D. Savage, J. F. Gallagher, Y. Ida and P. T. M. Kenny, Inorg. Chem. Commun. 5, 1034-1040 (2002).
  2. Synthesis and Structural Characterization of Redox-Responsive N Ferrocenoyl Amino Acid Esters; the X-ray Crystal Structure of N-Ferrocenoyl Alanine Methyl Ester; Electrochemical Anion Recognition and 1H NMR complexation studies. M. J. Sheehy, J. F. Gallagher, M. Yamashita, Y. Ida, J. White Colangelo, J. Johnson, R. Orlando and P. T. M. Kenny, J. of Organometallic Chemistry, 689, 1511-1520 (2004).
  3. Synthesis and structural characterization of novel N-para-ferrocenyl benzoyl amino acid ethyl esters and the X-ray crystal structures of the glycyl and (±)-2-aminobutyric acid derivative Fc-C6H4CONHCH(C2H5)CO2Et. D. Savage, G. Malone, J. F. Gallagher, Y. Ida and P. T. M. Kenny, J. of Organometallic Chemistry, 690, 383-393 (2005).
  4. The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters. D. Savage, N. Neary, G. Malone, S. R. Alley, J. F. Gallagher and P. T. M. Kenny, Inorg. Chem. Commun. 8, 429-432 (2005).
  5. The synthesis and structural characterization of N-ortho-ferrocenyl benzoyl amino acidesters. The X-ray crystal structure of N {ortho (ferrocenyl)benzoyl} L phenylalanine ethyl ester. D. Savage, G. Malone, S. R. Alley, J. F. Gallagher, A. Goel, P. N. Kelly, H. Mueller-Bunz and P. T. M. Kenny, J. of Organometallic Chemistry, (in press).