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Dartmouth College Department of Chemistry

 


Gordon W. Gribble

Dartmouth Professor of Chemistry

Professor Gribble received his B.S. degree in Chemistry in 1963 from the University of California, Berkeley, and his Ph.D. in Organic Chemistry in 1967 from the University of Oregon. After spending a year at UCLA as a National Cancer Institute Postdoctoral Fellow, he joined the faculty of Dartmouth College in 1968. Dr. Gribble has been a National Institutes of Health Research Career Development Awardee (1971-76), a National Science Foundation Professional Development Awardee (1977-78), and an American Cyanamid Academic Achievement Awardee (1988). In 2005 he was named to the endowed Chair “The Dartmouth Professor of Chemistry.”  He is the co-editor of “Progress in Heterocyclic Chemistry” and the co-author of “Palladium in Heterocyclic Chemistry.”

Selected Publications

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ggribble@dartmouth.edu

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Research Interests

Professor Gribble's research programs involve several areas of organic chemistry, most of which involve synthesis: biologically active natural products, novel indole chemistry, anticancer triterpenoid synthesis, new synthetic methodology, and novel radical and cycloaddition chemistry of heterocycles. Of prime interest is the synthesis of plant indole alkaloids that are potent anticancer or antibiotic agents.  Current work in this area is focused on ellipticine, vobasine, marine alkaloids, indolocarbazoles, and the zwitterionic alkaloids such as sempervirine. Thus, for example, several years ago Dr. Gribble developed a highly efficient synthesis of ellipticine, a derivative of which is currently used to treat several forms of human cancer.  In the area of new synthetic methodology, Dr. Gribble and his students have been investigating the chemistry of nitroindoles.  A newer area of research is the synthesis and biological activity of triterpenoids in the chemoprevention of cancer and diseases related to inflammation.  Two of these synthetic triterpenoids are currently in Phase 1 clinical trials for the treatment of cancer.




 


Selected Publications

  • “Nucleophilic Amination of 2-Iodo-3-nitro-1-(phenylsulfonyl)indole”; Roy, S.; Gribble, G.W. Tetrahedron Lett. 2007, 48, 1003-1007.
  • "4,6-Diphenyl-1-(phenylsulfonyl)-1H-furo[3,4-b]pyrrole"; Moskalev, N.V.; Gribble, G.W.; Jasinski, J.P. Acta Cryst. 2007, E63, o1279-o1281.
  • “Synthesis of a Novel N-Nitroalkyl Bisindolylmaleimide”; Roy, S.; Gribble, G.W. Synth. Commun. 2007, 37, 1879-1876.
  • “Convenient Synthesis of Bis(3-indolyl)acetylene via Sonogashira Coupling”; Roy, S.; Gribble, G.W. Synth. Commun. 2007, 37, 829-837.
  • “Pharmacodynamic Characterization of Chemopreventive Triterpenoids as Exceptionally Potent Inducers of Nrf2-Regulated Genes”; Yates, M.S.; Tauchi, M.; Katsuoka, F.; Flanders, K.C.; Liby, K.T.; Honda, T.; Gribble, G.W.; Johnson, D.A.; Johnson, J.A.; Burton, N.C.; Guilarte, T.R.; Yamamoto, M.; Sporn, M.B.; Kensler, T.W. Mol. Cancer Ther. 2007, 6, 154-162.
  • "Palladium in Heterocyclic Chemistry. A Guide for the Synthetic Chemist, 2nd Edition"; Li, J.J.; Gribble, G.W.; Elsevier, Amsterdam, 2007.
  • "3-Nitro-1-(phenylsulfonyl)indole"; Roy S.; Pelkey, E.T.; Gribble, G.W.; Jasinski, J.P. Acta Cryst. 2007, E63, o1829-o1831.
  • "Azepinyl 2-Bromo-1-methyl-1H-indol-3-yl Ketone"; Fraser, H.L.; Badenock, J.C.; Gribble, G.W.; Jasinski, J.P. Acta Cryst. 2007, E63, o2480-o2481.
  • “The Synthetic Triterpenoid TP-222 Inhibits RANKL Stimulation of Osteoclastogenesis and Matrix Metalloproteinase-9 Expression”; Fava, R.; Elliott, S.; Raymond, L.; Mollmark, J.; Hays, E.; Honda, T.; Gribble, G.W.; Sporn, M.B.; Vincenti, M.P. J. Rheumatol. 2007, 34, 1058-1068.
  • “The Synthetic Triterpenoids CDDO-Methyl Ester and CDDO-Ethyl Amide Prevent Lung Cancer Induced by Vinyl Carbamate in A/J Mice”; Liby, K.; Royce, D.B.; Williams, C.R.; Risingsong, R.; Yore, M.M.; Honda, T.; Gribble, G.W.; Dmitrovsky, E.; Sporn, T.A.; Sporn, M.B. Cancer Res. 2007, 67, 2414-2419.
  • “Novel Tricyclic Compounds Having Acetylene Groups at C-8a and Cyano Enones in Rings A and C:  Highly Potent Anti-inflammatory and Cytoprotective Agents”; Honda, T; Sundararajan, C; Yoshizawa, H; Su, X; Honda, Y; Liby, K.T.; Sporn, M. B.; Gribble, G.W. J. Med. Chem. 2007, 50, 1731-1734.
  • “1,3-Dipolar Cycloaddition of 2- and 3-Nitroindoles with Azomethine Ylides. A New Approach to Pyrrolo[3,4-b]indoles”; Roy, S.; Kishbaugh, T.L.S.; Jasinski, J.P.; Gribble, G.W. Tetrahedron Lett. 2007, 48, 1313-1316.
  • “Parameters Determining the Relative Efficacy of Hydroxynaphthoquinone Inhibitors of the Cytochrome bc1 Complex”; Kessl, J.J.; Moskalev, N.V.; Gribble, G.W.; Nasr, M.; Meshnick, S.R.; Trumpower, B.L. Biochim. Biophys. Acta – Bioenergetics 2007, 1767, 319-326.
  • “Novel Semisynthetic Analogues of Betulinic Acid with Diverse Cytoprotective, Antiproliferative, and Proapoptotic Activities”; Liby, K.; Honda, T.; Williams, C.R.; Risingsong, R.; Royce, D.B.; Suh, N.; Dinkova-Kostova, A.T.; Stephenson, K.K.; Talalay, P.; Sundararajan, C.; Gribble, G.W.; Sporn, M.B. Mol. Cancer Ther. 2007, 6, 2113-2119.