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Dr. John T. Gupton

Floyd D. and Elisabeth S. Gottwald Professor of Chemistry
Gottwald Science Center, N-301
University of Richmond, VA 23173
phone: (804) 287-6498
E-mail: jgupton@richmond.edu

Courses

Research Projects and Selected Publications

J. Gupton, S. Clough ,C. Hickenboth*, I. Bluhn Chertudi*, S. Cutro*, S. Petrich, F. Hicks*, D. Wilkinson* and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Regiocontrolled Preparation of Heterocyclic Appended Pyrazoles", Tetrahedron, 58, 5467-5474 (2002).

J. Gupton, S. Clough, R. Miller, J. Lukens*, C. Henry*, R. Kanters and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Synthesis of Ningalin B Hexamethyl Ether", Tetrahedron, 59, 207-215 (2003).

H. Yamanaka, K. Kase, M. Katayama, T. Ishihara, T. Konno and J. Gupton, "Reaction of b-Trifluoroethoxy Vinamidinium Salts with Carbon Nucleophiles", J. of Fluorine Chem., 120, 33-39 (2003).

B. Burnham, M. Evans, D. Smith, J. Holub, A. Argenti, M. Hoff, G. Daglish, D. Wilson, B. Taylor, J. Berkowitz, K. Krumpe, J. Gupton, T. Scarlett, R. Durham and I. Hall, "Synthesis and Cytotoxicity of Substituted Ethyl 2-Phenacyl-3-phenylpyrrole-4- carboxylates", Arch. Pharm. Pharm. Med. Chem., 336, 181-190 (2003).

S. Clough, J. Gupton, K. Griffin*, A. Hewitt*, M. Hudson*, A. Ilgali*, S. Mulcahey*, M. Roberts*, R. Miller and B. Norwood, "Extension of β-Chloroenals to Ethyl 5-Chloro-2,4-pentadienoates Using Wadsworth-Emmons Reactions: Subsequent Conversions to 5-Aryl-5-chloro-2,4-pentadienoic Acids and 5-Aryl-2-penten-4-ynoic Acids", Tetrahedron, 60, 10165-10169 (2004).

J. Gupton, R. Miller, S. Clough, K. Krumpe, E. Banner, R. Kanters, K. Du, K. Keertikar, N. Lauerman*, J. Solano*, B. Adams*, D. Callahan*, B. Little*, A. Scharf* and J. Sikorski, " The Application of Vinylogous Iminium Salt Derivatives to an Efficient Relay Synthesis of the Pyrrole Containing Alkaloids Polycitone A and B", Tetrahedron, 61, 1845-1854 (2005).

S. Clough, J. Gupton, A. Ligali*, M. Roberts*, D. Driscoll*, S. Annet*, A. Hewitt*, M. Hudson*, E. Jackson*, R. Miller, B. Norwood, R. Kanters, H. Wyre* and H. Petruzzi*, "Reactions of (Z)-3-Aryl-3-chloropropenals with Nucleophiles: Stereoselective Formation of (E)-Vinylogous Esters, (E)-Vinylogous Amides and Vinamidinium Salts", Tetrahedron, 61, 7554-7561 (2005).

J. Gupton, E. Banner, A. Scharf*, B. Norwood, R. Kanters, R. Dominey, J. Hempel*, A. Kharlamova*, I. Bluhn-Chertudi*, C. Hickenboth*, B. Little*, M. Coppock*, K. Krumpe, B. Burnham, H. Holt., K. Du, K. Keertikar, A. Diebes, S. Ghassemi and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to an Efficient Synthesis of the Pyrrole Containing Alkaloids Rigidin and Rigidin E", Tetrahedron, 62, 8243-8255 (2006).

S. Arimitsu, T. Konno, T. Ishihara, H. Yamanaka and J. Gupton, "Synthetic Application of Fluorinated Vinamidinium Salts: Synthesis of Fluorinated 1,3-butadienylphosphonates by the Reaction With Horner-Wadsworth-Emmons Reagents", J. of Fluorine Chem., 127, 1235-1241 (2006).

J. Gupton, "Pyrrole Natural Products with Antitumor Properties", Chapter. 2, pp 53-92  in "Heterocyclic Antitumor Antibiotics: Topics in Heterocyclic Chemistry, Vol.2", Ed. by M. Lee, Springer-Verlag, Berlin/Heidelberg, 2006: ISBN # 3-540-30982-9. 

J. Gupton, E. Banner, A. Scharf*, B. Norwood, R. Kanters, R. Dominey, J. Hempel*, A. Kharlamova*, I. Bluhn-Chertudi*, C. Hickenboth*, B. Little*, M. Coppock*, K. Krumpe, B. Burnham, H. Holt., K. Du, K. Keertikar, A. Diebes, S. Ghassemi and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to an Efficient Synthesis of the Pyrrole Containing Alkaloids Rigidin and Rigidin E", Tetrahedron, 62, 8243-8255 (2006).

S. Mooberry, K. Wiederhold, S. Dakshanamurthy, E. Hamel, E. Banner, A. Kharlamova*, J. Hempel*, J. Gupton and M. Brown,  "Identification and Characterization of a New Tubulin-Binding Tetrasubstituted Brominated Pyrrole", Molecular Pharmacology, 72 (1), 132-140 (2007).

C. Arthur, J. Gupton, G. Kellog, A. Yeudall and D. Gewirtz, "Autophagic Cell Death, Polyploidy and Senescence Induced in Breast Tumor Cells by the Substituted Pyrrole JG-03-14, a Novel Microtubule Poison", Biochemical Pharmacology, 74, 981-991 (2007).

A. Tripathi, M. Fornabaio, G. Kellogg, J. Gupton, D. Gewirtz, W. Yeudall, N. Vega and  S. Mooberry,    "Docking and Hydropathic Scoring of Polysubstituted Pyrrole Compounds with Anti-Tubulin Activity", Biorganic and Medicinal Chemistry, 16, #5, 2235-2242 (2008)..

J. Gupton, E. Banner, M. Sartin*, M. Coppock* J. Hempel*, A. Kharlamova*, D. Fisher*, B. Giglio*, K. Smith*, M. Keough*, T. Smith, R. Kanters, R. Dominey and J. Sikorski, "Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products", Tetrahedron, 64, 5246-5243 (2008).

J. Gupton, B. Giglio*, J. Eaton*, E. Rieck*, K. Smith*, M. Keough*, P. Barelli*, L. Firich*, J. Hempel*,T. Smith and R. Kanters, R., "The Application of Vinylogous Iminium Salt Derivatives to Efficient Formal Syntheses of the Marine Alkaloids Lamellarin G trimethylether and Ningalin B", Tetrahedron,65, 4283-4292 (2009).

N. Dalyot-Herman, F. Delgado-Lopez, D. Gewirtz, J. Gupton and E. Schwartz, "Interference with Endothelial Cell Function by JG-03-14, an Agent That Binds to the Colchicine Site on Microtubules", Biochemical Pharmacology,78(#9), 1167-1177 (2009).

J. Gupton, N. Telang, X. Jia*, B. Giglio*, J. Eaton*, P. Barelli*, M. Hovaizi*, K. Hall*, S. Welden*, M. Keough*, E. Worral*l, K. Finzel*, E. Kluball*, R. Kanters, S. Smith, S. Nunes*, M. Wright* and J. Birnstihl, "Further Studies on Vinamidinium Salt Amine Exchange Reactions, Borohydride Reductions and Subsequent Transformations", Tetrahedron, 66, 8485-8493 (2010).

J. Gupton, N. Telang, E.Banner, E. Kluball*, K. Hall*, K. Finzel*, X. Jia*, S. Bates*, S. Welden*, B. Giglio*, J. Eaton*, P. Barelli*, L. Firich*, J. Stafford*, M. Coppock*, E. Worrall*, R. Kanters, K. Keertikar and R. Osterman, "The Application of (Z)-Haloenoic Acids to the Synthesis of (Z)-5-Benzylidene-4-arylpyrrol-2(5H)-ones", Tetrahedron,  66, 9133-9122 (2010).

Chenxiao Da, Nakul Telang, Peter Barelli*, Xin Jia*, John T. Gupton, Susan L. Mooberry, and Glen Kellogg, "Pyrrole-Based Antitubulin Agents: Two Distinct Binding Modalities are Predicted for C-2 Analogs in the Colchicine Site", ACS Med. Chem. Lett., 3, 53-57 (2012).

J. Biggers, T. Nguyen, X. Di, J. Gupton, S. Henderson, Emery, S., Alotaibi, M., White, K., Almenera, J. and D. Gewirtz, "Autophagic Cell Death and Sustained Senescence Arrest in B16/F10 Melanoma Cells and HCT 116 Colon Carcinoma Cells in Response to the Novel Microtubule Poison, JG-03-14", Cancer Chemotherapy and Pharmacology", 71, 441-455 (2013).

Chenxiao Da, Nakul Telang, Kayleigh Hall*, Emily Kluball*, Peter Barelli*, Kara Finzel*, Xin Jia*, John T. Gupton, Susan L. Mooberry and Glen E. Kellogg, "Developing novel C-4 analogues of pyrrole-based antitubulin agents: weak but critical hydrogen bonding in the colchicine site", Med. Chem. Commun., 4, 417-421 (2013).

J. Gupton, N. Telang, D. Gazzo*, P. Barelli*, K. Lescalleet*, J. Fagan*, B. Mills*, K. Finzel*, R. Kanters, K. Crocker*, S. Dudek*, C. Lariviere*, S. Smith, K. Keetrikar, C. Warme and W. Zhong., "Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles", Tetrahedron,69, 5829-5840 (2013).

 

C. Da, S. Mooberry, J. Gupton and G. Kellogg, "How to Deal with Low Resolution Target Structures: Using SAR, Ensemble Docking, Hydropathic Analysis and 3D-QSAR to Definitively Map the α,β-Tubulin Colchicine Site", J. Med. Chem., 56,7382-7395 (2013).

 

J. Gupton, N. Telang, M. Wormald*, K. Lescalleet*, J. Patteson*, W. Curry*, A. Harrison*, M. Hoerrner*, J. Sobieski*, M. Kimmel*, E. Kluball* and T. Perry*, “Formal Group Activation of a Bromopyrrole Ester in Suzuki Cross-Coupling Reactions: Application to a Formal Synthesis of Polycitone A and B and Polycitrin A”, Tetrahedron,70, 2738-2745 (2014).

        *Denotes UR undergraduate student

Personal Information


Chemistry Faculty

Chemistry Department

University of Richmond