Dr. John Gupton

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 Ningaline B Hexamethyl Ether", Tetrahedron, 59, 207-215 (2003).

H. Yamanaka, K. Kase, M. Katayama, T. Ishihara, T. Konno and J. Gupton, "Reaction of ß-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. Scarleet, 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. Ligali*, S. Mulcahey*, M. Roberts*, R. Miller and B. Norwood, "Extension of ß-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. Annett*, 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).

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, 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. Worral*l, 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).

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).

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).

J. Gupton, N. Telang, J. Patteson*, K. Lescalleet*, S. Yeudall*, J. Sobieski*, A. Harrison* and W. Curry*, "The Application of Formyl Group Activation of Bromopyrrole Esters to Formal Syntheses of Lycogarubin C, Permethyl Storniamide and Lamellarin G Trimethyl Ether", Tetrahedron, 70, 9759-9767 (2014).

C. Rohena, N. Telang, C. Da, A. Risinger, J. Sikorski, G. Kellogg, J. Gupton and S. Mooberry,”Biological Characterization of an Improved Pyrrole-Based Colchicine Site Agent Identified Through Structure-Based Design”,  Mol. Pharm., 89, 287-296 (2016)

J. Ciemniecki*, C. Lewis*, J. Gupton and K. Fischer-Stenger, “Effects of a Pyrrole-Based, Microtubule-Depolymerizing Compound  on RAW 264.7 Macrophages”, Chemico-Biological Interactions, 246, 63-68, (2016).

J.Gupton, S. Yeudall, N. Telang, M. Hoerrner, E. Huff, E. Crawford, K. Lounsbury, M. Kimmel, W. Curry, A. Harrison, W. Juekun, A. Shimozono, J. Ortolani, K. Lescalleet, J. Patteson, V. Moore-Stoll, C. Rohena, S. Mooberry, A. Obaidullah, G. Kellogg and J. Sikorski, “Ortho Group Activation of a Bromopyrrole Ester in Suzuki-Miyaura Cross-coupling Reactions:Application to the Synthesis of New Microtubule Deploymerizing Agents with Potent Cytoxic Activities”, Bioorg. Med. Chem.,25  3206-3214 (2017).

S. Gilmore*, A. Gonye*, E. Li*, S. Reyes*, J. Gupton, O. Quintero, K. Stenger, “Effects of a Novel Microtubule-depolymerizer on Pro-inflammatory Signaling in RAW264.7 Macrophages”, Chemico-Biological Interactions, 280, 109-116, (2018).

J. Gupton, A. Shimozono*, E. Crawford*, J. Ortolani*, E. Clark*, M. Mahoney*, C. Heese*, J. Noble*, C.P. Mandry*, R. Dominey, E. Goldman, J. Sikorski and D. Fisher, “Further Studies on the the Application of Vinylogous Amides and β-Halovinylhalides to the Regiospecific Synthesis of Unysmmetrical, Polyfunctionalized 2,3,4- and 1,2,3,4-Substituted Pyrroles”, Tetrahedron, 74. 2650-2663, (2018).

G. Kellogg, C. Da., A. Tripathi, J. Gupton, N. Telang, J.Sikorski, S. Mooberry, C. Rohena, “Polysubstituted Pyrroles Having Microtubule-Disrupting, Cytotoxic and Antitumor Activities and Methods of Use Thereof”, U.S. Patent #9,944,597, April 17, 2018.

Gupton, E. Crawford,*M. Mahoney,* E. Clark,* W. Curry,* A. Lane,* A. Shomozono,* V. Moore-Stoll,* K. Elofson,* W. Juekeun, M. Newton,* S. Yeudall,* E. Jaekle,* R. Kanters and J. Sikorski, "Application of Vinylogous Carbamates and Vinylogous Aminonitriles to the Regiospecific Synthesis of Uniquely Functionalized Pyrroles and Quinolones", Tetrahedron, 74, 7408-7420, (2018). 

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.