Dr Daniel Whelligan
Lecturer in Organic/Medicinal Chemistry
Qualifications: MSci, PhD
Email: d.whelligan@surrey.ac.uk
Room no: 36 AZ 03
Further information
Biography
Daniel Whelligan gained his first degree (1st class) in Natural Sciences from the University of Cambridge (Churchill College) in 2000. After graduation, he spent the summer at Université Bordeaux I, France carrying out organic synthesis in the group of Professor Stephane Quideau. He then moved to the University of Durham for his PhD with Dr Patrick Steel on the use of silenes (Si=C) in novel organic synthetic methods. In 2004, he secured an Alexander von Humboldt Postdoctoral Research Fellowship to work on the use of paracyclophanes in asymmetric catalysis with Professor Carsten Bolm at RWTH Aachen University, Germany. From 2006-7, he took time to travel around the world including a 3 month postdoctoral research placement with Professor Mark von Itzstein at the Institute for Glycomics, Griffith University, Australia. On return to the UK, Daniel worked from 2007-10 at the Institute of Cancer Research (ICR) as a Postdoctoral Training Fellow in Medicinal Chemistry in the group of Dr Swen Hoelder on the discovery of inhibitors of cancer targets. In 2011 he was appointed as Lecturer of Organic/Medicinal Chemistry at the University of Surrey.
Research Interests
Drug discovery and design.
Novel organic synthetic methods to aid drug discovery and design.
Publications
Journal articles
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(2012) 'Synthesis of amino-substituted indoles using the Bartoli reaction'. Org Biomol Chem, 10 (22), pp. 4441-4447.doi: 10.1039/c2ob25256b
- . (2012) 'Planar-Chiral Bis-silanols and Diols as H-Bonding Asymmetric Organocatalysts'. European Journal of Organic Chemistry, , pp. 3373-3376.
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(2010) 'Aminopyrazine Inhibitors Binding to an Unusual Inactive Conformation of the Mitotic Kinase Nek2: SAR and Structural Characterization'. Journal of Medicinal Chemistry, 53 (21), pp. 7682-7698.doi: 10.1021/jm1008727Full text is available at: http://epubs.surrey.ac.uk/235558/
Abstract
We report herein the first systematic exploration of inhibitors of the mitotic kinase Nek2. Starting from HTS hit aminopyrazine 2, compounds with improved activity were identified using structure-based design. Our structural biology investigations reveal two notable observations. First, 2 and related compounds bind to an unusual, inactive conformation of the kinase which to the best of our knowledge has not been reported for other types of kinase inhibitors. Second, a phenylalanine residue at the center of the ATP pocket strongly affects the ability of the inhibitor to bind to the protein. The implications of these observations are discussed, and the work described here defines key features for potent and selective Nek2 inhibition, which will aid the identification of more advanced inhibitors of Nek2.
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(2010) 'Two-Step Synthesis of Aza- and Diazaindoles from Chloroamino-N-heterocycles Using Ethoxyvinylborolane'. The Journal of Organic Chemistry, 75 (1), pp. 11-15.doi: 10.1021/jo902143fFull text is available at: http://epubs.surrey.ac.uk/235557/
Abstract
An efficient two-step route to a broad range of aza- and diazaindoles was established, starting from chloroamino-N-heterocycles, without the need for protecting groups. The method involves an optimized Suzuki-Miyaura coupling with (2-ethoxyvinyl)borolane followed by acetic acid-catalyzed cyclization.
- . (2006) 'The synthesis of pseudo-geminal, pseudo-ortho and ortho hydroxy-oxazolinyl[2.2]paracyclophanes for use as ligands in asymmetric catalysis'. Adv Synth Catal, 348 (15), pp. 2093-2100.
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(2006) 'Synthesis of pseudo-geminal-, pseudo-ortho-, and ortho-phosphinyl-oxazolinyl-[2.2]paracyclophanes for use as ligands in asymmetric catalysis.'. American Chemical Society J Org Chem, 71 (12), pp. 4609-4618.doi: 10.1021/jo060668hFull text is available at: http://epubs.surrey.ac.uk/227185/
Abstract
Syntheses of three regioisomers of aromatic-substituted phosphinyl-oxazolinyl-[2.2]paracyclophanes, pseudo-geminal, pseudo-ortho, and ortho, have been carried out or, in the latter two cases, newly developed. It has, therefore, been demonstrated that all aromatic-substituted isomers relevant for use as chelating ligands for asymmetric catalysis are accessible. These P,N-ligands, along with their diastereoisomers, were shown to exhibit widely differing activity and enantioselectivity (up to 89% ee) in the Pd-catalyzed asymmetric allylic alkylation reaction.
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(2004) 'Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping.'. Org Biomol Chem, 2 (16), pp. 2381-2392.doi: 10.1039/B404166F
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(2004) 'Stereochemistry of the reaction of Si-phenyl silenes with butadienes: elaboration of the silacycloadducts to provide a novel route to substituted lactones.'. Org Biomol Chem, England: 2 (16), pp. 2393-2402.doi: 10.1039/B404175E
- . (2003) 'Silenes as novel synthetic reagents: synthesis of diols and lactones from simple alkyldienes'. Tetrahedron Lett, 44 (51), pp. 9135-9138.
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(2003) 'Novel one-pot synthesis of aryltris(trimethylsilyl)silanes.'. J Org Chem, 68 (8), pp. 3337-3339.doi: 10.1021/jo0268660
- . (2001) 'Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation'. Tetrahedron Lett, 42 (42), pp. 7393-7396.
Book chapters
- . (2009) 'Benzotriazole Linker Units'. in Scott PJH (ed.) Linker Strategies in Solid-Phase Organic Synthesis Wiley Article number 11
Teaching
Level 5 (Year 2) CHE2029 Medicinal Chemistry I
Level 6 (Year 3) CHE3046 Topics in Organic Chemistry
Level 6 (Year 3) CHE3049 Medicinal Chemistry II
Level 7 (Year 4) CHEM025 Advanced Topics in Organic Chemistry
Level 7 (Year 4) CHEM032 Advanced Medicinal Chemistry
Lecture notes, coursework, supplementary videos and documents available on SurreyLearn
