Lecturer in Medicinal Chemistry
5 West - 2.49B
Email: L.Caggiano@bath.ac.uk
Tel: +44 (0) 1225 385709
Dr Lorenzo Caggiano
Profile
Research Interests
The central focus of the group is to achieve the efficient synthesis of biologically active small molecules, using known and new synthetic methodologies.
Basic synthetic steps are often used to make elegant molecules; we wish to establish a programme of research using elegant chemistry to synthesise basic molecules, which have been shown to display potent biological activities.
Structural complexity does not necessarily correlate with biological activity...
Efficient synthesis of simplified natural product analogues
An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3•OEt2 to generate various lactams shown below, which display interesting biological activities.
We are now investigating the use of this methodology in the synthesis of simplified analogues of various natural products, such as pancratistatin and narciclasine. These natural products exhibit potent anti-cancer and anti-viral activities, however they cannot be obtained in sufficient quantities either by total synthesis or isolation from the natural source to be considered as a drug candidates. Therefore the efficient synthesis of simplified analogues that retain potency are of great interest.
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Publications
Ciupa, A., De Bank, P. A., Mahon, M. F., Wood, P. J. and Caggiano, L., 2013. Synthesis and antiproliferative activity of some 3-(pyrid-2-yl)-pyrazolines. MedChemComm, 4 (6), pp. 956-961.
Tunbridge, G. A., Baruchello, R. and Caggiano, L., 2013. Mild and efficient capture and functionalisation of CO2 using silver(I) oxide and application to 13C-labelled dialkyl carbonates. RSC Advances, 3 (14), pp. 4613-4621.
Ciupa, A., Mahon, M., De Bank, P. and Caggiano, L., 2012. Simple pyrazoline and pyrazole “turn on” fluorescent sensors selective for Cd2+ and Zn2+ in MeCN. Organic and Biomolecular Chemistry, 10 (44), pp. 8753-8757.
Ciupa, A., Griffiths, N. J., Light, S. K., Wood, P. J. and Caggiano, L., 2011. Design, synthesis and antiproliferative activity of urocanic-chalcone hybrid derivatives. MedChemComm, 2 (10), pp. 1011-1015.
Judd, K. E. and Caggiano, L., 2011. Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives. Organic and Biomolecular Chemistry, 9 (14), pp. 5201-5210.
Judd, K. E., Mahon, M. F. and Caggiano, L., 2009. Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates. Synthesis, 2009 (16), pp. 2809-2817.
Nolasco, L., Perez Gonzalez, M., Caggiano, L. and Jackson, R. F. W., 2009. Application of Negishi Cross-Coupling to the Synthesis of the Cyclic Tripeptides OF4949-III and K-13. Journal of Organic Chemistry, 74 (21), pp. 8280-8289.
Drago, C., Walker, E. J., Caggiano, L. and Jackson, R. F. W., 2009. Enantioselective oxidation of an alkyl aryl sulfide. Organic Syntheses, 86, pp. 121-129.
Caggiano, L., Jackson, R. F. W., Meijer, A. J. H. M., Pickup, B. T. and Wilkinson, K. A., 2008. Ionisation of the zinc/iodine bond of alkylzinc iodides in dimethylformamide from theory and experiment. Chemistry - A European Journal, 14 (29), p. 8798.
Oswald, C. L., Carrillo-Marquez, T., Caggiano, L. and Jackson, R. F. W., 2008. Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides. Tetrahedron, 64 (4), pp. 681-687.
Bartrum, H. E., Adams, H., Caggiano, L. and Jackson, R. F. W., 2008. Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions. Tetrahedron, 64 (17), pp. 3701-3712.
Loghmani-Khouzani, H., Poorheravi, M. R., Sadeghi, M. M. M., Caggiano, L. and Jackson, R. F. W., 2008. α-Fluorination of β-ketosulfones by Selectfluor™ F–TEDA–BF4. Tetrahedron, 64 (30-31), pp. 7419-7425.
