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Professor Jim Iley

Profile summary

  • Central Academic Staff
  • Professor of Medicinal Chemistry
  • Faculty of Science, Technology, Engineering & Mathematics
  • School of Life, Health & Chemical Sciences
  • jim.iley

Professional biography

I re-joined the Open University in August 2014 to lead the development of one of the new Level 1 science modules, S112. Outside my OU role I currently sit on the Institute for Apprenticeships Quality Assurance Committee.

From 2010 till 2014, I was Executive Director for Science and Education for the Royal Society of Chemistry, and oversaw the development of the science, education and industry strategies. I am proud to have initiated the development of the award winning site, LearnChemistry www.rsc.org/learn-chemistry. Between 2012 and 2014 I sat on the board of SusChem, the European Technology Platform for sustainable chemistry, holding responsibility for education.

Before 2010, I spent a little over 30 years with the OU as a member of the Chemistry & Analytical Sciences Department, first as a lecturer, then senior lecturer and latterly as professor. From 2005 to 2008 I was Associate Dean in the Science Faculty for Course Production and from 2008-2010 was Head of the Chemistry & Analytical Sciences Department .

My research activity has been in the area of molecules of biological interest, on which I collaborated with colleagues at the Faculdade de Farmacia, Lisboa, Portugal for 30 years. In recognition for my work in helping to establish a medicinal chemistry research centre, in 2005 I was awarded an Honorary Doctorate from the Universidade de Lisboa.

I studied for both my first degree (BSc, 1976) and doctorate (PhD, 1979)  at Imperial College, London. My PhD thesis, on the reaction mechanisms of amides, phosphylamides and sulfonamides, was supervised by Brian Challis.

Research interests

My most recent research has focused on :

  • The metabolism of exogenous compounds by cytochrome P450 mono-oxygenase and related chemical systems; in particular, dialkyltriazenes – molecules that chemotherapeutic agents – and dialkylamides, N-alkylureas and nitriles – materials that are used in large scale as solvents

  • The chemistry of pro-drugs;  acyloxyalkyl-, aminoacyl-, dipeptidyl-, cysteinylmethyl-, and glycosylmethyl- carrier group systems for nitrogen- and oxygen-based functional groups, such as amines, amides, sulfonamides, triazenes, carboxylic acids

  • The design and synthesis of novel amino acids with functional side-chains, paricularly the synthesis of amino acids that carry a nucleic acid base in their side-chain .

Some publications related to my research interests are:  

  1. N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases, A B Santana, S D Lucas, L M Goncalves, H F Correia, T A F Cardote, R C Guedes, J Iley, R Moreira, Bioorg. Med. Chem Lett., 2012, 22, 3993-3997

  2. Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones, R C F Jones, A K Choudhury, J N Iley, M E Light, G Loizou, T A Pillainayagam, Beilstein J. Org. Chem., 2012, 8, 308-312

  3. A carbamate-based approach to primaquine prodrugs: Antimalarial activity, chemical stability and enzymatic activation, G Mata, V E do Rosario, J Iley, L Constantino, R Moreira, Bioorg. Med. Chem., 2012, 20, 886-892

  4. A new 3-(ethoxycarbonylmethyl)isoxazolopyridone as a precursor to acylpyridones, R C F Jones, J N Iley, G Loizou, Heterocycles, 2012, 84,1235-1244

  5. Synthesis, stability, biochemical and pharmacokinetic properties of a new potent and selective 4-oxo-beta beta-lactam inhibitor of human leukocyte elastase, J Mulchande, S I Simões, M M Gaspar, C V Eleuterio, R Oliveira, M E M Cruz, R Moreira, J Iley, J. Enz. Inhibit. Med. Chem., 2011, 26,169-175

  6. Basic hydrolysis of quinolinyl N,N-dimethylcarbamates: a two-step mechanism, D Silva, F Norberto, S Santos, J Iley, J. Phys. Org. Chem., 2011, 24, 1081-1087

  7. Imidazolium ylides from a conjugate addition-proton transfer route and their cycloaddition reactions, R C F Jones, J N Iley, M Sanchis-Amat, X H Zhang, V McKee, S J Coles, T Gelbrich, Chem. Commun. 2011, 47, 7965-7967

  8. Novel heterocyclic alpha-amino acids with sulfur-containing side-chains, R C F Jones, L J Crumpling, J N Iley, ARKIVOC, 2011,82-103

  9. Dopamine- and tyramine-based derivatives of triazenes. Activation by tyrosinase and implications for prodrug design, M J Perry, E Mendes, A L Simplício, A Coelho, J Iley, R Moreira, and A P Francisco, Eur. J Med. Chem. 2009, 44, 3228–3234

  10. Towards an efficient prodrug of the alkylating metabolite monomethyltriazene: synthesis and stability of N-acylamino acid derivatives of triazenes, M J Perry, E Carvalho, E Rosa and J Iley,  Eur. J. Med. Chem., 2009, 44, 1049-1056
     
                
 

 

Teaching interests

These lie in the fields of organic, medicinal and biological chemistry. I have taught from first year undergraduate through to doctoral training courses, and have devised and developed distance learning materials for:

  • the strategy of organic synthesis;
  • carbonyl chemistry;
  • oxidation and reduction;
  • biosynthesis;
  • energy transformations in biological systems;
  • drug development and synthesis;
  • GABA, benzodiazepines and barbiturates;
  • ß-lactams;
  • cancer chemotherapy;
  • inflammation;
  • drugs that target enzyme/receptor binding;
  • ion channels and drugs that target ion channels

I am currently interested in developing electronic and online media for learning. At undergraduate level I have developed an interactive DVD sequence on The Interpretation of 1H-NMR Spectra, and at Masters Level have used forums to develop a Virtual Weekend school. I am particularly attracted to the use of problem based learning in the science curriculum, and wish to explore ways in which this approach can be incorporated into the distance learning environment.

 

Publications

New insights on repellent recognition by Anopheles gambiae odorant-binding protein 1 (2018-04-03)
Tzotzos, George; Iley, Jim N. and Moore, Elaine A.
PLoS ONE, 13, Article e0194724(4)

New methodologies for the synthesis of 3-acylpyridone metabolites (2010-03)
Jones, Raymond C. F.; Choudhury, Abdul K.; Iley, James N.; Loizou, Georgia; Lumley, Christopher and McKee, Vickie
Synlett(4) (pp. 654-658)

Reaction of Naphthoquinones with Substituted Nitromethanes. Facile Synthesis and antifungal activity of Naphtho[2,3-d]isoxazole-4,9-diones (2010)
Santos, Maria M.M.; Faria, Natália; Iley, Jim; Coles, Simon J.; Hursthouse, Michael B.; Martins, M. Luz and Moreira, Rui
Bioorganic and Medicinal Chemistry Letters, 20(1) (pp. 193-195)

4-Oxo-β-lactams (Azetidine-2,4-diones) Are Potent and Selective Inhibitors of Human Leukocyte Elastase (2010)
Mulchande, Jalmira; Oliveira, Rudi; Carrasco, Marta; Gouveia, Luís; Guedes, Rita C.; Iley, Jim and Moreira, Rui
Journal of Medicinal Chemistry, 53(1) (pp. 241-253)

Rational design, synthesis, biophysical and antiproliferative evaluation of fluorenone derivatives with DNA G-quadruplex binding properties (2010)
Alcaro, Stefano; Artese, Anna; Iley, James N.; Missailidis, Sotiris; Ortuso, Francesco; Parrotta, Lucia; Pasceri, Raffaele; Paduano, Francesco; Sissi, Claudia; Trapasso, Francesco and Vigorita, Maria Gabriella
ChemMedChem, 5(4) (pp. 575-583)

A catalytic dipolar cycloaddition route to pyrroloimidazoles (2009-07)
Jones, Raymond C.F.; Iley, James N.; Sanchis-Amat, Maria; Zhan, Xiaohui and Elsegood, Mark R.J.
Tetrahedron Letters, 50(26) (pp. 3577-3579)

The characterisation of flavone-DNA isoform interactions as a basis for anticancer drug development (2009-06)
Ragazzon, Patricia A.; Bradshaw, Tracey; Matthews, Charlie; Iley, Jim and Missailidis, Sotiris
Anticancer Research, 29 (pp. 2273-2283)

Structure-activity studies of the binding of the flavonoid scaffold to DNA (2009-06)
Ragazzon, Patricia A.; Iley, Jim and Missailidis, Sotiris
Anticancer Research, 29(6) (pp. 2285-2293)

Synthesis of the Pyoverdin Chromophore by a Biomimetic Oxidative Cyclization (2009-03-04)
Jones, Raymond C.F.; Yau, Sze Chak; Iley, James N.; Smith, Janet E.; Dickson, James; Elsegood, Mark R.J.; McKee, Vickie and Coles, Simon J.
Organic Letters, 11(7) (pp. 1519-1522)

Towards an efficient prodrug of the alkylating metabolite monomethyltriazene: Synthesis and stability of N-acylamino acid derivatives of triazenes (2009)
Perry, Maria de Jesus; Carvalho, Emília; Rosa, Eduarda and Iley, Jim
European Journal of Medicinal Chemistry, 44(3) (pp. 1049-1056)

Dopamine- and tyramine-based derivatives of triazenes. Activation by tyrosinase and implications for prodrug design (2009)
Perry, M. J.; Mendes, E.; Simplício, A. L.; Coelho, A.; Iley, J.; Moreira, R. and Francisco, A. P.
European Journal of Medicinal Chemistry, 44(8) (pp. 3228-3234)

Unanticipated acyloxymethylation of sumatriptan indole nitrogen atom and its implications in prodrug design (2008-06)
Rodrigues, Tiago; Moreira, Rui; Guedes, Rita C.; Iley, Jim and Lopes, Francisca
Archiv der Pharmazie, 341(6) (pp. 344-350)

Azetidine-2,4-diones (4-oxo-beta-lactams) as scaffolds for designing elastase inhibitors (2008)
Mulchande, J.; Guedes, R. C.; Tsang, W.-Y.; Page, M. I.; Moreira, R. and Iley, J.
Journal of Medicinal Chemistry, 51(6) (pp. 1783-1790)

The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors (2007-08-01)
Moreira, Rui; Valente, Claudia; Guedes, Rita C.; Iley, Jim; Jaffar, Mohammed and Douglas, Kenneth T.
Bioorganic and Medicinal Chemistry, 15(15) (pp. 5340-5350)

Tetraplex DNA specific ligands based on the fluorenone-carboxamide scaffold (2007-05-01)
Alcaro, Stefano; Artese, Anna; Iley, James N.; Maccari, Rosanna; Missailidis, Sotiris; Ortuso, Francesco; Ottana, Rosaria; Ragazzon, Patricia and Vigorita, Maria Gabriella
Bioorganic and Medicinal Chemistry Letters, 17(9) (pp. 2509-2514)

Crystallization and Preliminary Diffraction Studies of Porcine Pancreatic Elastase in Complex with a Novel Inhibitor (2007-01)
Oliveira, Tânia F.; Mulchande, Jalmira; Moreira, Rui; Iley, Jim and Archer, Margarida
Protein and Peptide Letters, 14(1) (pp. 93-95)

Aminocarbonyloxymethyl ester prodrugs of flufenamic acid and diclofenac: suppressing the rearrangement pathway in aqueous media (2007-01)
Ribeiro, Lina; Silva, Nuno; Iley, Jim; Rautio, Jarkko; Järvinen, Tomi; Mota-Filipe, Hélder; Moreira, Rui and Mendes, Eduarda
Archiv der Pharmazie, 340(1) (pp. 32-40)

An alkylation route to carbo- and heteroaromatic amino acids (2007)
Jones, Raymond C.F.; Berthelot, Didier J.C. and Iley, James N.
Arkivoc(11) (pp. 73-84)

Intermolecular 1,3-dipolar cycloadditions of azomethine imines (2007)
Jones, Raymond C.F.; Hollis, Stephen J. and Iley, James N.
Arkivoc(5) (pp. 152-166)

Kinetics and mechanism of hydrolysis of benzimidazolylcarbamates (2007)
Norberto, F.P.; Santos, S.P.; Iley, J.; Silva, D.B. and Corte Real, M.
Journal of the Brazilian Chemical Society, 18(1) (pp. 171-178)

The efficiency of C-4 substituents in activating the -lactam scaffold towards serine proteases and hydroxide ion (2007)
Mulchande, Jalmira; Martins, Luísa; Moreira, Rui; Archer, Margarida; Oliveira, Tania F. and Iley, Jim
Organic and Biomolecular Chemistry, 5 (pp. 2617-2626)

Reactivity of imidazolidin-4-one derivatives of primaquine: implications for prodrug design (2006-10-16)
Chambel, Paula; Capela, Rita; Lopes, Francisca; Iley, Jim; Morais, Jose; Gouveia, Luıs; Gomes, Jose R. B.; Gomes, Paula and Moreira, Rui
Tetrahedron, 62(42) (pp. 9883-9891)

Mechanism of hydrolysis of substituted N-thiazolylcarbamate esters in OH- solutions (2006-10)
Araujo, M. E. M.; Norberto, F.; Pamplona, T. and Iley, J.
Journal of Chemical Research, 2006(10) (pp. 664-667)

Dipeptide vinyl sultams: Synthesis via the Wittig–Horner reaction and activity against papain, falcipain-2 and Plasmodium falciparum (2006-08-01)
Valente, Claudia; Guedes, Rita C.; Moreira, Rui; Iley, Jim; Gut, Jiri and Rosenthal, Philip J.
Bioorganic and Medicinal Chemistry Letters, 16(15) (pp. 4115-4119)

The Bsmoc group as a novel scaffold for the design of irreversible inhibitors of cysteine proteases (2006-05-15)
Iley, Jim; Moreira, Rui; Martins, Luisa; Guedes, Rita C. and Soares, Claudio M.
Bioorganic and Medicinal Chemistry Letters, 16(10) (2738 -2741)

Monofluorinated di- and tetrahydropyrans via Prins-type cyclisations (2006)
Pivnevi, Levan; Dobbs, Adrian P.; Penny, Mark J.; Martinović, Sasa; Iley, James N. and Stephenson, Peter T.
Chemical Communications (pp. 3134-3136)

Intramolecular 1,3-dipolar cycloadditions of dihydroimidazolium ylides: synthesis of pyrrolo[1,2,3-de]quinoxalines and imidazo[1,2-a]indoles (2006)
Lory, Pedro M.J.; Jones, Raymond C.F.; Iley, James N.; Coles, Simon J. and Hursthouse, Michael B.
Organic and Biomolecular Chemistry, 4 (pp. 3155-3165)

Development of anti MUC1 DNA aptamers for the imaging and radiotherapy of breast cancer (2006)
Da Pieve, C.; Iley, J. N.; Perkins, A. and Missailidis, S.
Breast Cancer Research, 8 (pp. 15-16)

Design of an anti MUC1 DNA aptamer as novel radiopharmaceutical for the diagnostic imaging and targeted radiotherapy of tumours (2006)
Da Pieve, C.; Bactyari, A.; Perkins, A.; Missailidis, S. and Iley, J.
European Journal of Cancer Supplements, 4(12) (pp. 65-66)

Design, Synthesis, and Enzymatic Evaluation of N1-Acyloxyalkyl- and N1-Oxazolidin-2,4-dion-5-yl-Substituted beta-lactams as Novel Inhibitors of Human Leukocyte Elastase (2005-07)
Moreira, Rui; Santana, Ana Bela; Iley, Jim; Neres, Joao; Douglas, Kenneth T.; Horton, Peter N. and Hursthouse, Michael B.
Journal of Medicinal Chemistry, 48(15) (pp. 4861-4870)

Imidazolidin-4-one derivatives of primaquine as novel transmission-blocking antimalarials (2005-01)
Araújo, Maria Joao; Bom, Joana; Capela, Rita; Casimiro, Catarina; Chambel, Paula; Gomes, Paula; Iley, Jim; Lopes, Francisca; Morais, Jose; Moreira, Rui; de Oliveira, Eliandre; do Rosário, Virgilio and Vale, Nuno
Journal of Medicinal Chemistry, 48 (pp. 888-892)

The mechanism of hydrolysis of aryl ether derivatives of 3-hydroxymethyltriazenes (2005)
Carvalho, Emilia; Francisco, Ana Paula; Iley, Jim and Rosa, Eduarda
European Journal of Organic Chemistry, 2005(10) (pp. 2056-2063)

Amidomethylation of amodiaquine: antimalarial N-Mannich base derivatives (2004-10-04)
Lopes, Francisca; Capela, Rita; Gonçaves, Jose O.; Horton, Peter N.; Hursthouse, Michael B.; Iley, Jim; Casimiro, Catarina M.; Bom, Joana and Moreira, Rui
Tetrahedron Letters, 45(41) (7663 -7666)

Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations (2004-06-21)
Gomes, Paula; Araújo, Maria J.; Rodrigues, Manuela; Vale, Nuno; Azevedo, Zelia; Iley, Jim; Chambel, Paula; Morais, Jose and Moreira, Rui
Tetrahedron, 60(26) (pp. 5551-5562)

Kinetics and mechanism of hydrolysis of N-acyloxymethyl derivatives of azetidin-2-one (2004-04)
Valente, Emilia; Gomes, J. Richard. B.; Moreira, Rui and Iley, Jim
Journal of Organic Chemistry, 69 (pp. 3359-3367)

Oxidation of tertiary benzamides by 5,10,15,20-tetraphenylporphyrinatoiron (III) chloride – tert-butylhydroperoxide (2004)
Constantino, Luis and Iley, Jim
Organic and Biomolecular Chemistry, 2(13) (pp. 1894-1900)

Synthesis, stability and in vitro dermal evaluation of Aminocarbonyloxymethyl Esters as prodrugs of Carboxylic Acid Agents (2002-03)
Mendes, Eduarda; Furtado, Tania; Neres, Joao; Iley, Jim; Jarvinen, Tomi; Rautio, Jarkko and Moreira, Rui
Bioorganic and Medicinal Chemistry, 10(3) (pp. 809-816)

Synthesis of some new 2-heterosubstituted 4,5-dihydroimidazoles (2002)
Jones, Raymond C. F.; Iley, James N. and Lory, Pedro M. J.
Arkivoc(6) (pp. 152-163)

Inactivation of rat liver cytochrome P450 (P450) by N,N-dimethylformamide and N,N-dimethylacetamide (2001-10-15)
Tolando, Roberto; Zanovella, Alberta; Ferrara, Roberta; Iley, Jim N. and Manno, Maurizzio
Toxicology Letters, 124(1-3) (pp. 101-111)

Synthesis by conjugate radical addition of new heterocyclic amino acids with nucleobase side chains (2001-07-23)
Jones, Raymond C. F.; Berthelot, Didier J.C. and Iley, James N.
Tetrahedron, 57(30) (pp. 6539-6555)

Pyrrolo[1,2,3-de]quinoxalines: unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides (2001-06-04)
Jones, Raymond C. F.; Iley, James N.; Lory, Pedro M. J.; Coles, Simon C.; Light, Mark E. and Hursthouse, Michael B.
Tetrahedron Letters, 42(23) (pp. 3951-3954)

Design, synthesis and stability of N-acyloxymethyl- and N-aminocarbonyloxymethyl-2-azetidinones as human leukocyte elastase inhibitors (2001-04-23)
Clemente, A.; Domingos, A.; Grancho, A. P.; Iley, James; Moreira, R.; Neres, J.; Palma, N.; Santana, A. B. and Valente, E.
Bioorganic and Medicinal Chemistry Letters, 11(8) (pp. 1065-1068)

Chemical and microsomal oxidation of tertiary amides: regio-and stereoselective aspects (2001)
Iley, Jim; Tolando, Roberto and Constantino, Luis
Journal of the Chemical Society: Perkin Transactions 2 (pp. 1299-1305)

Kinetics and mechanism of N-amidomethylsulfonamides (2001)
Iley, James; Lopes, Francisca and Moreira, Rui
Journal of the Chemical Society: Perkin Transactions 2(5) (pp. 749-753)

Hydrolysis of aryl N-methyl-N-arenesulfonylcarbamates (2001)
Araújo, M. Eduarda M.; Campelo, Margarida; Iley, Jim and Norberto, Fatima
Journal of the Chemical Society: Perkin Transactions 2 (pp. 494-497)

Anti-heparanase aptamers as inhibitors of angiogenesis and tissue remodelling (2009)
Simmons, Suzanne; Brenchley, P. E. C.; Iley, James; McKenzie, E. A.; Velasco, Maria and Missailidis, Sotiris
In : YSL Networking Angiogenesis Conference (14 Jul 2009)

Development of anti-MUC1 DNA aptamers for the imaging of breast cancer (2008-05-13)
Da Pieve, C.; Iley, J. N.; Perkins, A. and Missailidis, S.
In : EACR20 (5-8 Jul 2008, Lyon, France)

DNA aptamers as novel radiopharmaceuticals for imaging and targeted radiotherapy of epithelial tumours (2006)
Da Pieve, C.; Bakhtyari, A.; Perkins, A. C.; Iley, J. and Missailidis, S.
In : European Association of Nuclear Medicine '06 (30 Sep - 04 Oct 2006, Athens, Greece)

Novel DNA-binding chemotherapeutic agents based on flavonoid scaffolds (2005)
Ragazzon, P.; Iley, J. N. and Missailidis, S.
In : NCRI Cancer Conference (2-5 Oct 2005, Birmingham, U.K.)

Development of novel DNA-binding chemotherapeutic agents based on flavonoid scaffolds of active ingredients isolated from Chinese herbal remedies (2004)
Ragazzon, Patricia; Iley, James and Missailidis, Sotiris
In : CNIO Cancer Conference: Structural Biology of Cancer Targets (19-22 Sep 2004, Madrid, Spain)

Structure-activity related studies between the flavonoid skeleton and DNA duplex, triplex and tetraplex structures (2004)
Ragazzon, P.; Iley, J. N. and Missailidis, S.
In : Frontiers in Chemical Biology: The Chemical Biology of Cancer (8-10 Sep 2004)

Molecular encounters between active ingredients from herbal remedies and DNA (2003)
Ragazzon, P.; Iley, J. N. and Missailidis, S.
In : Fourth European Workshop in Drug Design (4EWDD) (25 May - 01 Jun 2003, Siena, Italy)