Towards the Synthesis of Biologically Important Heterocycles Claire Mc Donnell Support Mentors: Anna Przybyl and Sarah Rawe. Background:
Heterocyclic compounds are composed of rings that contain carbon atoms in addition to an atom (or atoms)
other than carbon. Aromatic heterocycles are of significant interest due to their presence in advanced
pharmaceutical agents, for example, Plavix, a blockbuster drug used in the treatment of vascular diseases [1],
and Lipitor, which lowers cholesterol levels. They also have applications as materials and oligomeric
thiophenes have been employed as diodes and semi conductors [2].
Both 3-nitropyrroles and 3-nitrothiophenes can be used as building blocks for the synthesis of porphyrins,
whose electronic and optical properties can be altered by incorporation of electron donating and electron
withdrawing group [3]. In addition, synthesis of core-modified porphyrins, where one or more nitrogen atoms
are replaced by sulfur atoms, can improve the efficiency of porphyrins as photosensitizers in photodynamic
The aim of this work is to synthesise and characterise some heterocyclic compounds which are of interest due
to their biological applications. They may include certain isoquinolines, dipyrrins, dipyrromethanes, porphyrins
Methodology:
(i) Synthesis of a range of biologically important heterocycles using multistep routes.
(ii) Purification by recrystallisation or flash column chromatography of all synthetic intermediates and
(iii) Characterization using spectroscopic techniques of all synthetic intermediates and products.
Learning outcomes:
The training provided will provide a firm grounding for a future career in academia or industry and graduates
with these skills are highly sought after.
By the end of the project the student will be able to:
• Apply organic synthetic and purification techniques to multi-step syntheses of biologically important
• Discuss the principles and application of spectroscopic analysis of these compounds by IR, NMR and
UV-VIS spectroscopy and, time permitting, Mass Spectrometry.
• Demonstrate improved communication, record-keeping, scientific report writing and problem-solving
skills, an appreciation how to approach and undertake scientific research and be aware of the opportunities
Benefits to Research Group:
The project will contribute to the work of several researchers in the Material Synthesis and Applications lab in
the FOCAS Institute and their collaborators. Initial research in relation to some aspects of the project is
underway at a postgraduate level and this project will support aspects of this ongoing work. The studies
proposed will allow the knowledge already gained at DIT to be applied to the synthesis and characterisation of
additional interesting heterocycles and will contribute to the body of knowledge in this area.
[1] P. Savi, J. M. Pereillo, M. F. Uzabiaga, J. Combalbert; C. Picard, J. P. Maffrand, M. Pascal, J. M. Herbert,
Thromb. Haemostasis 2000, 84, 891–896.
[2] P. B. Dervan, Bioorg. Med. Chem., 2001, 9, 2215
[3] E. G. A. Notaras, M. Fazekas , J. J. Doyle, W. J. Blau, M. O. Senge, Chem. Comm. 2007, 2166
[4] J.-H. Ha, S. Ko, C.-H. Lee, W.-Y. Lee, Y.-R. Kim, Chem. Phys. Lett. 2001, 349, 271
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Towards the Synthesis of Biologically Important Heterocycles