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Volumn 18, Issue 10, 2016, Pages 616-624

Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles

Author keywords

1,2,4 oxadiazoles; carboxylic acids; nitriles; one pot parallel synthesis; readily accessible (REAL) arrays

Indexed keywords

AMIDOXIME; CARBOXYLIC ACID; G PROTEIN COUPLED RECEPTOR; NITRILE; OXADIAZOLE DERIVATIVE; OXIME; PIFEXOLE;

EID: 84991238126     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscombsci.6b00103     Document Type: Article
Times cited : (22)

References (51)
  • 2
    • 84887369429 scopus 로고    scopus 로고
    • Identification of Novel IGF1R Kinase Inhibitors by Molecular Modeling and High-Throughput Screening
    • Moriev, R.; Vasylchenko, O.; Platonov, M.; Grygorenko, O.; Volkova, K.; Zozulya, S. Identification of Novel IGF1R Kinase Inhibitors by Molecular Modeling and High-Throughput Screening Acta Naturae 2013, 5, 90-99
    • (2013) Acta Naturae , vol.5 , pp. 90-99
    • Moriev, R.1    Vasylchenko, O.2    Platonov, M.3    Grygorenko, O.4    Volkova, K.5    Zozulya, S.6
  • 5
    • 84959386977 scopus 로고    scopus 로고
    • 4-Acyl Pyrrole Derivatives Yield Novel Vectors for Designing Inhibitors of the Acetyl-Lysine Recognition Site of BRD4(1)
    • Hügle, M.; Lucas, X.; Weitzel, G.; Ostrovskyi, D.; Breit, B.; Gerhardt, S.; Einsle, O.; Günther, S.; Wohlwend, D. 4-Acyl Pyrrole Derivatives Yield Novel Vectors for Designing Inhibitors of the Acetyl-Lysine Recognition Site of BRD4(1) J. Med. Chem. 2016, 59, 1518-1530 10.1021/acs.jmedchem.5b01267
    • (2016) J. Med. Chem. , vol.59 , pp. 1518-1530
    • Hügle, M.1    Lucas, X.2    Weitzel, G.3    Ostrovskyi, D.4    Breit, B.5    Gerhardt, S.6    Einsle, O.7    Günther, S.8    Wohlwend, D.9
  • 9
    • 84903303681 scopus 로고    scopus 로고
    • One-Pot Parallel Synthesis Approach to Secondary Amines Based on the Reductive Amination of Ketones
    • Bogolubsky, A.; Moroz, Y.; Pipko, S.; Panov, D.; Konovets, A.; Doroschuk, R.; Tolmachev, A. One-Pot Parallel Synthesis Approach to Secondary Amines Based on the Reductive Amination of Ketones Synthesis 2014, 46, 1765-1772 10.1055/s-0033-1341226
    • (2014) Synthesis , vol.46 , pp. 1765-1772
    • Bogolubsky, A.1    Moroz, Y.2    Pipko, S.3    Panov, D.4    Konovets, A.5    Doroschuk, R.6    Tolmachev, A.7
  • 10
    • 0001815816 scopus 로고    scopus 로고
    • Introduction: Frontiers in Organic Synthesis
    • Wender, P. A. Introduction: Frontiers in Organic Synthesis Chem. Rev. 1996, 96, 1-2 10.1021/cr9500803
    • (1996) Chem. Rev. , vol.96 , pp. 1-2
    • Wender, P.A.1
  • 11
    • 84934825506 scopus 로고    scopus 로고
    • Phenoxymethyl 1,3-Oxazoles and 1,2,4-Oxadiazoles as Potent and Selective Agonists of Free Fatty Acid Receptor 1 (GPR40)
    • Zahanich, I.; Kondratov, I.; Naumchyk, V.; Kheylik, Y.; Platonov, M.; Zozulya, S.; Krasavin, M. Phenoxymethyl 1,3-Oxazoles and 1,2,4-Oxadiazoles as Potent and Selective Agonists of Free Fatty Acid Receptor 1 (GPR40) Bioorg. Med. Chem. Lett. 2015, 25, 3105-3111 10.1016/j.bmcl.2015.06.018
    • (2015) Bioorg. Med. Chem. Lett. , vol.25 , pp. 3105-3111
    • Zahanich, I.1    Kondratov, I.2    Naumchyk, V.3    Kheylik, Y.4    Platonov, M.5    Zozulya, S.6    Krasavin, M.7
  • 13
    • 0035837067 scopus 로고    scopus 로고
    • Antimycobacterial Activity of Substituted Isosteres of Pyridine- and Pyrazinecarboxylic Acids. 2. 1
    • Gezginci, M. H.; Martin, A. R.; Franzblau, S. G. Antimycobacterial Activity of Substituted Isosteres of Pyridine- and Pyrazinecarboxylic Acids. 2. 1 J. Med. Chem. 2001, 44, 1560-1563 10.1021/jm000350w
    • (2001) J. Med. Chem. , vol.44 , pp. 1560-1563
    • Gezginci, M.H.1    Martin, A.R.2    Franzblau, S.G.3
  • 17
    • 84865491027 scopus 로고    scopus 로고
    • The Developability of Heteroaromatic and Heteroaliphatic Rings - Do Some Have a Better Pedigree as Potential Drug Molecules than Others?
    • Ritchie, T. J.; Macdonald, S. J. F.; Peace, S.; Pickett, S. D.; Luscombe, C. N. The Developability of Heteroaromatic and Heteroaliphatic Rings-Do Some Have a Better Pedigree as Potential Drug Molecules than Others? MedChemComm 2012, 3, 1062-1069 10.1039/c2md20111a
    • (2012) MedChemComm , vol.3 , pp. 1062-1069
    • Ritchie, T.J.1    Macdonald, S.J.F.2    Peace, S.3    Pickett, S.D.4    Luscombe, C.N.5
  • 18
    • 0029046233 scopus 로고
    • Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics
    • Borg, S.; Estenne-Bouhtou, G.; Luthman, K.; Csoeregh, I.; Hesselink, W.; Hacksell, U. Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics J. Org. Chem. 1995, 60, 3112-3120 10.1021/jo00115a029
    • (1995) J. Org. Chem. , vol.60 , pp. 3112-3120
    • Borg, S.1    Estenne-Bouhtou, G.2    Luthman, K.3    Csoeregh, I.4    Hesselink, W.5    Hacksell, U.6
  • 20
    • 0035910989 scopus 로고    scopus 로고
    • Parallel Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acids Using an Improved, Uronium-Based, Activation
    • Poulain, R. F.; Tartar, A. L.; Déprez, B. P. Parallel Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acids Using an Improved, Uronium-Based, Activation Tetrahedron Lett. 2001, 42, 1495-1498 10.1016/S0040-4039(00)02293-0
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1495-1498
    • Poulain, R.F.1    Tartar, A.L.2    Déprez, B.P.3
  • 21
    • 84924538340 scopus 로고    scopus 로고
    • One-Pot Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acids Using 4-(Dimethylamino)pyridinium Acetate as Efficient, Regenerable, and Green Catalyst with Ionic Liquid Character
    • Nowrouzi, N.; Khalili, D.; Irajzadeh, M. One-Pot Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acids Using 4-(Dimethylamino)pyridinium Acetate as Efficient, Regenerable, and Green Catalyst with Ionic Liquid Character J. Iran. Chem. Soc. 2015, 12, 801-806 10.1007/s13738-014-0542-3
    • (2015) J. Iran. Chem. Soc. , vol.12 , pp. 801-806
    • Nowrouzi, N.1    Khalili, D.2    Irajzadeh, M.3
  • 22
    • 68049114670 scopus 로고    scopus 로고
    • 2: An Efficient Catalyst for the Synthesis of 1,2,4-Oxadiazoles from Amidoximes and Organic Nitriles
    • 2: An Efficient Catalyst for the Synthesis of 1,2,4-Oxadiazoles from Amidoximes and Organic Nitriles J. Org. Chem. 2009, 74, 5640-5643 10.1021/jo900818h
    • (2009) J. Org. Chem. , vol.74 , pp. 5640-5643
    • Augustine, J.K.1    Akabote, V.2    Hegde, S.G.3    Alagarsamy, P.4
  • 23
    • 84941145428 scopus 로고    scopus 로고
    • 1,2,4- and 1,3,4-Oxadiazole Synthesis by Palladium-Catalyzed Carbonylative Assembly of Aryl Bromides with Amidoximes or Hydrazides
    • Andersen, T. L.; Caneschi, W.; Ayoub, A.; Lindhardt, A. T.; Couri, M. R. C.; Skrydstrup, T. 1,2,4- and 1,3,4-Oxadiazole Synthesis by Palladium-Catalyzed Carbonylative Assembly of Aryl Bromides with Amidoximes or Hydrazides Adv. Synth. Catal. 2014, 356, 3074-3082 10.1002/adsc.201400487
    • (2014) Adv. Synth. Catal. , vol.356 , pp. 3074-3082
    • Andersen, T.L.1    Caneschi, W.2    Ayoub, A.3    Lindhardt, A.T.4    Couri, M.R.C.5    Skrydstrup, T.6
  • 24
    • 84957840719 scopus 로고    scopus 로고
    • Copper-Catalyzed Direct Synthesis of 1,2,4-Oxadiazoles from Amides and Organic Nitriles by Oxidative N-O Bond Formation
    • Kuram, M. R.; Kim, W. G.; Myung, K.; Hong, S. Y. Copper-Catalyzed Direct Synthesis of 1,2,4-Oxadiazoles from Amides and Organic Nitriles by Oxidative N-O Bond Formation Eur. J. Org. Chem. 2016, 2016, 438-442 10.1002/ejoc.201501502
    • (2016) Eur. J. Org. Chem. , vol.2016 , pp. 438-442
    • Kuram, M.R.1    Kim, W.G.2    Myung, K.3    Hong, S.Y.4
  • 25
    • 84894056703 scopus 로고    scopus 로고
    • Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles and Their Behavior of Liquid Crystallines
    • Guo, J.; Hua, R.; Sui, Y.; Cao, J. Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles and Their Behavior of Liquid Crystallines Tetrahedron Lett. 2014, 55, 1557-1560 10.1016/j.tetlet.2014.01.066
    • (2014) Tetrahedron Lett. , vol.55 , pp. 1557-1560
    • Guo, J.1    Hua, R.2    Sui, Y.3    Cao, J.4
  • 26
    • 0001472969 scopus 로고
    • Ueber Amidoxime und Azoxime
    • Tiemann, F.; Krüger, P. Ueber Amidoxime Und Azoxime Ber. Dtsch. Chem. Ges. 1884, 17, 1685-1698 10.1002/cber.18840170230
    • (1884) Ber. Dtsch. Chem. Ges. , vol.17 , pp. 1685-1698
    • Tiemann, F.1    Krüger, P.2
  • 28
    • 70349643110 scopus 로고    scopus 로고
    • Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine-Aplysinopsin Hybrid Molecule
    • Porwal, S.; Chauhan, S. S.; Chauhan, P. M. S.; Shakya, N.; Verma, A.; Gupta, S. Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine-Aplysinopsin Hybrid Molecule J. Med. Chem. 2009, 52, 5793-5802 10.1021/jm900564x
    • (2009) J. Med. Chem. , vol.52 , pp. 5793-5802
    • Porwal, S.1    Chauhan, S.S.2    Chauhan, P.M.S.3    Shakya, N.4    Verma, A.5    Gupta, S.6
  • 29
    • 84927164906 scopus 로고    scopus 로고
    • Discovery and Preliminary Evaluation of 2-Aminobenzamide and Hydroxamate Derivatives Containing 1,2,4-Oxadiazole Moiety as Potent Histone Deacetylase Inhibitors
    • Cai, J.; Wei, H.; Hong, K. H.; Wu, X.; Cao, M.; Zong, X.; Li, L.; Sun, C.; Chen, J.; Ji, M. Discovery and Preliminary Evaluation of 2-Aminobenzamide and Hydroxamate Derivatives Containing 1,2,4-Oxadiazole Moiety as Potent Histone Deacetylase Inhibitors Eur. J. Med. Chem. 2015, 96, 1-13 10.1016/j.ejmech.2015.04.002
    • (2015) Eur. J. Med. Chem. , vol.96 , pp. 1-13
    • Cai, J.1    Wei, H.2    Hong, K.H.3    Wu, X.4    Cao, M.5    Zong, X.6    Li, L.7    Sun, C.8    Chen, J.9    Ji, M.10
  • 31
    • 74549167367 scopus 로고    scopus 로고
    • 1-Ethyl-3-(3-Dimethylaminopropyl) Carbodiimide Hydrochloride (EDCI × HCl)
    • Goyal, N. 1-Ethyl-3-(3-Dimethylaminopropyl) Carbodiimide Hydrochloride (EDCI × HCl) Synlett 2010, 2010, 335-336 10.1055/s-0029-1219043
    • (2010) Synlett , vol.2010 , pp. 335-336
    • Goyal, N.1
  • 32
    • 84975744816 scopus 로고    scopus 로고
    • Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals
    • Dunetz, J. R.; Magano, J.; Weisenburger, G. A. Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals Org. Process Res. Dev. 2016, 20, 140-177 10.1021/op500305s
    • (2016) Org. Process Res. Dev. , vol.20 , pp. 140-177
    • Dunetz, J.R.1    Magano, J.2    Weisenburger, G.A.3
  • 33
    • 12044258245 scopus 로고
    • 1-Hydroxy-7-Azabenzotriazole. An Efficient Peptide Coupling Additive
    • Carpino, L. A. 1-Hydroxy-7-Azabenzotriazole. An Efficient Peptide Coupling Additive J. Am. Chem. Soc. 1993, 115, 4397-4398 10.1021/ja00063a082
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 34
    • 84981203310 scopus 로고    scopus 로고
    • Optimized Reaction Conditions for Amide Bond Formation in DNA-Encoded Combinatorial Libraries
    • Li, Y.; Gabriele, E.; Samain, F.; Favalli, N.; Sladojevich, F.; Scheuermann, J.; Neri, D. Optimized Reaction Conditions for Amide Bond Formation in DNA-Encoded Combinatorial Libraries ACS Comb. Sci. 2016, 18, 438-443 10.1021/acscombsci.6b00058
    • (2016) ACS Comb. Sci. , vol.18 , pp. 438-443
    • Li, Y.1    Gabriele, E.2    Samain, F.3    Favalli, N.4    Sladojevich, F.5    Scheuermann, J.6    Neri, D.7
  • 36
    • 84937424685 scopus 로고    scopus 로고
    • Structure-Based Design, Synthesis and Evaluation in Vitro of Arylnaphthyridinones, Arylpyridopyrimidinones and Their Tetrahydro Derivatives as Inhibitors of the Tankyrases
    • Kumpan, K.; Nathubhai, A.; Zhang, C.; Wood, P. J.; Lloyd, M. D.; Thompson, A. S.; Haikarainen, T.; Lehtiö, L.; Threadgill, M. D. Structure-Based Design, Synthesis and Evaluation in Vitro of Arylnaphthyridinones, Arylpyridopyrimidinones and Their Tetrahydro Derivatives as Inhibitors of the Tankyrases Bioorg. Med. Chem. 2015, 23, 3013-3032 10.1016/j.bmc.2015.05.005
    • (2015) Bioorg. Med. Chem. , vol.23 , pp. 3013-3032
    • Kumpan, K.1    Nathubhai, A.2    Zhang, C.3    Wood, P.J.4    Lloyd, M.D.5    Thompson, A.S.6    Haikarainen, T.7    Lehtiö, L.8    Threadgill, M.D.9
  • 37
    • 42449156380 scopus 로고    scopus 로고
    • Changing Requirements of Purification as Drug Discovery Programs Evolve from Hit Discovery
    • Isbell, J. Changing Requirements of Purification as Drug Discovery Programs Evolve from Hit Discovery J. Comb. Chem. 2008, 10, 150-157 10.1021/cc700152v
    • (2008) J. Comb. Chem. , vol.10 , pp. 150-157
    • Isbell, J.1
  • 38
    • 84898474395 scopus 로고    scopus 로고
    • Off-Rate Screening (ORS) by Surface Plasmon Resonance. An Efficient Method to Kinetically Sample Hit to Lead Chemical Space from Unpurified Reaction Products
    • Murray, J. B.; Roughley, S. D.; Matassova, N.; Brough, P. A. Off-Rate Screening (ORS) By Surface Plasmon Resonance. An Efficient Method to Kinetically Sample Hit to Lead Chemical Space from Unpurified Reaction Products J. Med. Chem. 2014, 57, 2845-2850 10.1021/jm401848a
    • (2014) J. Med. Chem. , vol.57 , pp. 2845-2850
    • Murray, J.B.1    Roughley, S.D.2    Matassova, N.3    Brough, P.A.4
  • 39
    • 84991217169 scopus 로고    scopus 로고
    • eMolecules
    • eMolecules. https://www.emolecules.com/#?click=screening-compounds.
  • 40
    • 84969545588 scopus 로고    scopus 로고
    • Docking Screens for Novel Ligands Conferring New Biology
    • Irwin, J. J.; Shoichet, B. K. Docking Screens for Novel Ligands Conferring New Biology J. Med. Chem. 2016, 59, 4103-4120 10.1021/acs.jmedchem.5b02008
    • (2016) J. Med. Chem. , vol.59 , pp. 4103-4120
    • Irwin, J.J.1    Shoichet, B.K.2
  • 42
    • 84869031561 scopus 로고    scopus 로고
    • Pfizer Global Virtual Library (PGVL): A Chemistry Design Tool Powered by Experimentally Validated Parallel Synthesis Information
    • Hu, Q.; Peng, Z.; Sutton, S. C.; Na, J.; Kostrowicki, J.; Yang, B.; Thacher, T.; Kong, X.; Mattaparti, S.; Zhou, J. Z. et al. Pfizer Global Virtual Library (PGVL): A Chemistry Design Tool Powered by Experimentally Validated Parallel Synthesis Information ACS Comb. Sci. 2012, 14, 579-589 10.1021/co300096q
    • (2012) ACS Comb. Sci. , vol.14 , pp. 579-589
    • Hu, Q.1    Peng, Z.2    Sutton, S.C.3    Na, J.4    Kostrowicki, J.5    Yang, B.6    Thacher, T.7    Kong, X.8    Mattaparti, S.9    Zhou, J.Z.10
  • 43
    • 84942531848 scopus 로고    scopus 로고
    • SCUBIDOO: A Large yet Screenable and Easily Searchable Database of Computationally Created Chemical Compounds Optimized toward High Likelihood of Synthetic Tractability
    • Chevillard, F.; Kolb, P. SCUBIDOO: A Large yet Screenable and Easily Searchable Database of Computationally Created Chemical Compounds Optimized toward High Likelihood of Synthetic Tractability J. Chem. Inf. Model. 2015, 55, 1824-1835 10.1021/acs.jcim.5b00203
    • (2015) J. Chem. Inf. Model. , vol.55 , pp. 1824-1835
    • Chevillard, F.1    Kolb, P.2
  • 44
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings Adv. Drug Delivery Rev. 1997, 23, 3-25 10.1016/S0169-409X(96)00423-1
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 45
    • 0037030653 scopus 로고    scopus 로고
    • Molecular Properties That Influence the Oral Bioavailability of Drug Candidates
    • Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates J. Med. Chem. 2002, 45, 2615-2623 10.1021/jm020017n
    • (2002) J. Med. Chem. , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.-Y.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 46
    • 77950571108 scopus 로고    scopus 로고
    • New Substructure Filters for Removal of Pan Assay Interference Compounds (PAINS) from Screening Libraries and for Their Exclusion in Bioassays
    • Baell, J. B.; Holloway, G. A. New Substructure Filters for Removal of Pan Assay Interference Compounds (PAINS) from Screening Libraries and for Their Exclusion in Bioassays J. Med. Chem. 2010, 53, 2719-2740 10.1021/jm901137j
    • (2010) J. Med. Chem. , vol.53 , pp. 2719-2740
    • Baell, J.B.1    Holloway, G.A.2
  • 47
    • 84948442908 scopus 로고    scopus 로고
    • ZINC 15 - Ligand Discovery for Everyone
    • Sterling, T.; Irwin, J. J. ZINC 15-Ligand Discovery for Everyone J. Chem. Inf. Model. 2015, 55, 2324-2337 10.1021/acs.jcim.5b00559
    • (2015) J. Chem. Inf. Model. , vol.55 , pp. 2324-2337
    • Sterling, T.1    Irwin, J.J.2
  • 48
    • 84893114019 scopus 로고    scopus 로고
    • Fast Balanced Sampling for Highly Stratified Population
    • Hasler, C.; Tillé, Y. Fast Balanced Sampling for Highly Stratified Population Comput. Stat. Data Anal. 2014, 74, 81-94 10.1016/j.csda.2013.12.005
    • (2014) Comput. Stat. Data Anal. , vol.74 , pp. 81-94
    • Hasler, C.1    Tillé, Y.2
  • 49
    • 84991198792 scopus 로고    scopus 로고
    • Chemistry Development Kit
    • Chemistry Development Kit. https://sourceforge.net/projects/cdk/.
  • 50
    • 0032546517 scopus 로고    scopus 로고
    • New Acetylene Based Histamine H3 Receptor Antagonists Derived from the Marine Natural Product Verongamine
    • Ali, S. M.; Tedford, C. E.; Gregory, R.; Yates, S. L.; Phillips, J. G. New Acetylene Based Histamine H3 Receptor Antagonists Derived from the Marine Natural Product Verongamine Bioorg. Med. Chem. Lett. 1998, 8, 1133-1138 10.1016/S0960-894X(98)00181-4
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1133-1138
    • Ali, S.M.1    Tedford, C.E.2    Gregory, R.3    Yates, S.L.4    Phillips, J.G.5
  • 51
    • 0025816212 scopus 로고
    • 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-A]pyrimidines as Agonists and Inverse Agonists at Benzodiazepine Receptors
    • Tully, W. R.; Gardner, C. R.; Gillespie, R. J.; Westwood, R. 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-A]pyrimidines as Agonists and Inverse Agonists at Benzodiazepine Receptors J. Med. Chem. 1991, 34, 2060-2067 10.1021/jm00111a021
    • (1991) J. Med. Chem. , vol.34 , pp. 2060-2067
    • Tully, W.R.1    Gardner, C.R.2    Gillespie, R.J.3    Westwood, R.4


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