Dr Mike Edwards

Title: Lecturer
Phone: (+44) 01782 7 33252
Email: m.g.edwards@keele.ac.uk
Location: Lennard-Jones 1.03
Role: Programme Director for Chemistry and Medicinal Chemistry
Contacting me: Try my office or make an appointment by email
Mike Edwards

I was appointed as a lecturer at Keele in the summer of 2011. I obtained first my undergraduate degree (MChem) from the University of Bath undertaking a final year project, synthesising  anti-malarial agents, under the supervision of Prof. Malcolm Sainsbury. Having loved my 4 years in Bath I stayed to complete a PhD working with Prof. Jon Williams. My research pioneered a new approach to C-C bond formation using alcohols as alkylating agents and transition metal catalysis to “borrow hydrogen” – this remains an area of worldwide research interest today.

Following this I undertook two postdoctoral research stints, first at the University of Illinois Urbana−Champaign (USA) working with Prof. Scott Denmark in the area of Lewis base catalysis and organoelement chemistry, and more recently with Prof Richard Taylor at the University of York working on the synthesis of natural products and biologically relevant heterocycles.

Our research is targeted in the broad area of molecular synthesis and its application. We aim to develop new and efficient methods to prepare interesting molecules and apply them to interesting problems, particularly in the area of medicinal chemistry.

1. Medicinal Chemistry and Biological Probes
(a) Targeted Autotaxin inhibitors as a therapy for Ovarian Cancer (in collaboration with Alan Richardson and Steve Allin)
Ovarian tumours represent a challenging drug target, many of the best chemotherapies displaying poor pharmacokinetic properties and undergoing extensive in vivo metabolism. We are examining methods for the effective treatment of such tumours by delivering inhibitors which target autotaxin (ATX), an enzyme which plays an important role in the proliferation of ovarian tumours. We recently reported a proof of concept study with the dendrimer-conjugate (1) to deliver the ATX inhibitor S32386, and are interested in novel analogues for ATX inhibition.

Dendrimer conjugates

 



(b) Novel Anti-malarial agents (in collaboration with Tess Phillips, Paul Horrocks and Steve Allin)
We are investigating the synthesis and evaluation of alkaloids based on an indole derived template which possess anti-malarial activity via a novel mechanism of action. Of current interest are β-carbolines (2) which can be prepared via classical Pictet-Spengler chemistry.

Beta-carbolines


(c) Novel Antioxidant Glutathione Peroxidase (GPx) Mimetics
The organoselenium heterocycle ebselen (3) is a mimic of the enzyme Glutathione Peroxidase (GPx), a key element in the body’s defence against reactive oxygen species (ROS) and oxidants. It has been investigated in phase III clinical trials for the treatment of reperfusion injury, but despite showing excellent in vitro activity it has limited in vivo activity. We are interested in the evaluation of alternative GPx mimetics based on selenium(IV) derivatives e.g. (4) which have an alternative mechanism of action.


2. Tandem Reactions, Heterocycles and Synthesis
(a) Electrocyclic reactions
Thermal electrocyclic ring closures e.g. (I) and (II), are useful reactions because of their predictable stereochemical outcomes, but are under utilised because of the difficulty in preparing the precursors such as triene 5. We are interesed in developing tandem reaction sequences that can access electrocyclisation precursors in order to apply them to the synthesis of interesting targets.

Thermal electrocyclic ring closure


(b) Synthesis of spiropyrans sensors (in collaboration with Aleks Radu as part of the Ionophore Based Sensors [IBS] network)
Spiropyrans such as 6, exist in equilibrium with their ring opened forms in solution. However, when exposed to light, the (Z)-alkene present in the molecule is isomerised reversibly to the (E)-alkene which can no longer ring close. These properties make them suitable for use as photosensors. We are investigating the development of suitable synthetic routes to prepare spiropyrans which can be applied as IBS.

Spiropyran photosensors


(c) Organolement Chemistry
Organosulfur, organoselenium and organophosphorus reagents have proven to be highly versatile reagents in organic synthesis over the previous 50 years. We are interested in the chemistry of these molecules and the control over reactivity they provide. Of current interest are bifunctional reagents built upon templates that utilise two organolement groups with a suitable linker, e.g. (7) to enable controlled bi-directional synthesis.

Bifunctional reagents

Selected Publications

  • Fisher N, Hilton-Bolt T, Edwards MG, Haxton KJ, McKenzie M, Allin SM, Richardson A. 2014. Dendrimer Conjugate of [4-(Tetradecanoylamino)benzyl]phosphonic Acid (S32826) as an Autotaxin Inhibitor. ACS Med Chem Lett, vol. 5(1), 34-39. link> doi>
  • Bastin R, Dale JW, Edwards MG, Papillon JPN, Webb MR, Taylor RJK. 2011. Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route. TETRAHEDRON, vol. 67(51), 10026-10044. link> doi>
  • Beltran-Rodil S, Edwards MG, Pugh DS, Reid M, Taylor RJK. 2010. The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. SYNLETT, 602-606. link> doi>
  • Catozzi N, Edwards MG, Raw SA, Wasnaire P, Taylor RJK. 2009. Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach. J Org Chem, vol. 74(21), 8343-8354. link> doi>
  • Beltran-Rodil S, Donald JR, Edwards MG, Raw SA, Taylor RJK. 2009. Tandem retro-aldol/Wittig/Michael and related cascade processes. TETRAHEDRON LETTERS, vol. 50(26), 3378-3380. link> doi>

Full Publications List show

Journal Articles

  • Fisher N, Hilton-Bolt T, Edwards MG, Haxton KJ, McKenzie M, Allin SM, Richardson A. 2014. Dendrimer Conjugate of [4-(Tetradecanoylamino)benzyl]phosphonic Acid (S32826) as an Autotaxin Inhibitor. ACS Med Chem Lett, vol. 5(1), 34-39. link> doi>
  • Bastin R, Dale JW, Edwards MG, Papillon JPN, Webb MR, Taylor RJK. 2011. Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route. TETRAHEDRON, vol. 67(51), 10026-10044. link> doi>
  • Beltran-Rodil S, Edwards MG, Pugh DS, Reid M, Taylor RJK. 2010. The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. SYNLETT, 602-606. link> doi>
  • Catozzi N, Edwards MG, Raw SA, Wasnaire P, Taylor RJK. 2009. Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach. J Org Chem, vol. 74(21), 8343-8354. link> doi>
  • Beltran-Rodil S, Donald JR, Edwards MG, Raw SA, Taylor RJK. 2009. Tandem retro-aldol/Wittig/Michael and related cascade processes. TETRAHEDRON LETTERS, vol. 50(26), 3378-3380. link> doi>
  • Edwards MG, Pugh DS, Whitwood AC, Taylor RJK. 2009. gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate. Acta Crystallogr C, vol. 65(Pt 2), o39-o41. link> doi>
  • Edwards MG, Paxton RJ, Pugh DS, Whitwood AC, Taylor RJK. 2008. gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. SYNTHESIS-STUTTGART, 3279-3288. link> doi>
  • Edwards MG, Kenworthy MN, Kitson RRA, Perry A, Scott MS, Whitwood AC, Taylor RJK. 2008. The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 4769-4783. link> doi>
  • Edwards MG, Paxton RJ, Pugh DS, Taylor RJK. 2008. An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate. SYNLETT, 521-524. link> doi>
  • Barfoot CW, Burns AR, Edwards MG, Kenworthy MN, Ahmed M, Shanahan SE, Taylor RJK. 2008. A convergent synthesis of the tricyclic core of the dictyosphaeric acids. Org Lett, vol. 10(2), 353-356. link> doi>
  • Edwards MG, Kenworthy MN, Kitson RRA, Scott MS, Taylor RJK. 2008. The telescoped intramolecular michael/olefination (TIMO) approach to alpha-alkylidene-gamma-butyrolactones: synthesis of (+)-paeonilactone B. Angew Chem Int Ed Engl, vol. 47(10), 1935-1937. link> doi>
  • Donald JR, Edwards MG, Taylor RJK. 2007. Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides. TETRAHEDRON LETTERS, vol. 48(30), 5201-5204. link> doi>
  • Black PJ, Edwards MG, Williams JMJ. 2006. Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 4367-4378. link> doi>
  • Denmark SE and Edwards MG. 2006. On the mechanism of the selenolactonization reaction with selenenyl halides. J Org Chem, vol. 71(19), 7293-7306. link> doi>
  • Black PJ, Cami-Kobeci G, Edwards MG, Slatford PA, Whittlesey MK, Williams JMJ. 2006. Borrowing hydrogen: iridium-catalysed reactions for the formation of C-C bonds from alcohols. Org Biomol Chem, vol. 4(1), 116-125. link> doi>
  • Black PJ, Edwards MG, Williams JMJ. 2005. Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols. TETRAHEDRON, vol. 61(5), 1363-1374. link> doi>
  • Edwards MG, Jazzar RFR, Paine BM, Shermer DJ, Whittlesey MK, Williams JMJ, Edney DD. 2004. Borrowing hydrogen: a catalytic route to C-C bond formation from alcohols. Chem Commun (Camb), 90-91. link> doi>
  • Adair GRA, Edwards MG, Williams JMJ. 2003. Triphenylphosphine-catalysed conversion of maleic anhydride into acrylate esters. TETRAHEDRON LETTERS, vol. 44(29), 5523-5525. link> doi>
  • Edwards MG and Williams JMJ. 2002. Catalytic electronic activation: indirect "Wittig" reaction of alcohols. Angew Chem Int Ed Engl, vol. 41(24), 4740-4743. link> doi>
  • Edwards MG, Phillips TR, Horrocks PD, Tunstall LV, Allin SMA. FORTHCOMING: Preparation and Anti-malarial activity of 2-Aminobenzimidazoles. TBC.
  • Phillips TR, Edwards MG, Horrocks PD, Allin SM, Tunstall LV. FORTHCOMING: Spiroindolines paper (title to be confirmed).
  • Fisher N, Edwards MG, Allin SM, McKenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. FORTHCOMING: Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate.
  • Fisher N, Edwards MG, Allin SM, McKenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. FORTHCOMING: Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate.
  • Phillips TR, Edwards MG, Horrocks P, Tunstall LV, Allin S. FORTHCOMING: Tetrahydro-beta-carbolines paper (title to be confirmed).

I teach on the Chemistry and Medicinal Chemistry degree programmes in the following modules:

  •     CHE-10048 - Practical and Professional Chemistry Skills 1
  •     CHE-10048 - Practical and Professional Chemistry Skills 2
  •     CHE-10050 - Chemical Properties and Reactions (Module Leader)
  •     CHE-20001 - Organic Synthesis and Chirality
  •     CHE-20027 - Medicinal and Biological Chemistry 1
  •     CHE-20031 - Structural Inorganic Chemistry
  •     CHE-30002 - Dual Honours Research Project
  •     CHE-30037 - Topics in Chemistry
  •     CHE-30039 - Advanced Organic Chemistry
  •     CHE-30040 - Chemistry Research Project
  •     CHE-30041 - Medicinal Chemistry Research Project
  •     CHE-30044 - Topics in Medicinal Chemistry
  •     CHE-30046 - Synoptic Topics in Chemistry (Module Leader)
  •     CHE-30047 - Medicinal and Biological Chemistry 2
  •     CHE-40021 - MChem Research Project
  •     CHE-40023 - Applied Chemistry Topics