Department of Medicinal Chemistry

 

Joseph E. Rice

Associate Professor of Medicinal Chemistry

Department of Medicinal Chemistry

Ernest Mario School of Pharmacy
Rutgers, The State University of New Jersey
160 Frelinghuysen Road
Piscataway, New Jersey 08854-8020
Phone: (848) 445-5382

FAX: (732) 445-6312
email: jrice@rci.rutgers.edu

Education:  Ph.D. (Organic Chemistry) 1982, Polytechnic Institute of New York

 

 


Research Interests

The focus of my research is organic synthesis as applied to the preparation of biologically-active molecules. I am particularly intrigued by the possibilities presented by the use of organometallic chemistry in synthesis. The utility of organometallic reagents for the rapid and stereoselective synthesis of advanced intermediates suitable for structure-activity investigations is an area of active research in my laboratory. Related to this is an interest in developing novel methods for preparing oxazoles and derivatizing existing oxazole rings. As these new methods are developed they will be employed in the synthesis of oxazole-containing natural products. Another area of interest is to employ the energy contained within small-ring compounds to drive the synthesis of biologically-important compounds.

 

Selected Publications

  • Blankson, G., Pilch, D.S., Liu, A.A., Liu, L.F., Rice, J.E., and LaVoie, E.J. Macrocyclic Biphenyl Tetraoxazoles: Synthesis, Evaluation as G-Quadruplex Stabilizers and Cytotoxic Activity. ACS Med. Chem. Lett., 2013 (Submitted).

  • Rzuczek, S.G., Pilch, D.S., Liu, A., Liu, L.F., LaVoie, E.J., and Rice, J.E. Macrocyclic pyridyl polyoxazoles:  Selective RNA and DNA G-quadruplex ligands as antitumor agents. J. Med. Chem., 53(9), 3632-3644, 2010.

  • Satyanarayana, M., Kim, Y-A., Rzuczek, S.G., Pilch, D.S., Liu, A.A., Liu, L.F., Rice, J.E., and LaVoie, E.J. Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity. Bioorg. Med. Chem. Lett., 20(10), 3150-3154, 2010.

    Tsai, Y-C., Qi, H., Lin, C-P., Lin, R-K., Kerrigan, J., Rzuczek, S.G., LaVoie, E.J., Rice, J.E., Pilch, D.S., and Liu, L.F. A G-quadruplex stabilizer induces M phase cell cycle arrest. J. Biol. Chem., 284(34), 22535-22543, 2009.
  • Satyanarayana, M., Rzuczek, S.G., LaVoie, E.J., Pilch, D.S., Liu, A., Liu, L.F., and Rice, J.E. Ring-closing metathesis for the synthesis of a highly G-quadruplex selective macrocyclic hexaoxazole having enhanced cytotoxic potency. Bioorg. Med. Chem. Lett., 18(13), 3802-3804, 2008.

  • Pilch, D.S., Barbieri, C.M., Rzuczek, S.G., LaVoie, E.J., and Rice, J.E. Targeting human telomeric G-quadruplex DNA with oxazole-containing macrocyclic compounds. Biochimie, 90(8), 1233-1249, 2008.
  • Rzuczek, S.G., Pilch, D.S., LaVoie, E.J., and Rice, J.E. Lysinyl macrocyclic hexaoxazoles: Synthesis and selective G-quadruplex stabilizing properties. Bioorg. Med. Chem. Lett., 18, 913-917, 2008.
  • Barbieri, C.M., Srinivasan, A.R., Rzuczek, S.G., Rice, J.E., LaVoie, E.J., and Pilch, D.S. Defining the mode, energetics and specificity with which a macrocyclic hexaoxazole binds to human telomeric G-quadruplex DNA. Nucleic Acids Res., 35(10), 3272-3286, 2007.
  • Minhas, G.S., Pilch, D.S., Kerrigan, J.E., LaVoie, E.J., and Rice, J.E. Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles. Bioorg. Med. Chem. Lett., 16, 3891-3895, 2006.
  • Lambert, J.D., Rice, J.E., Hong, J., Hou, Z., and Yang, C.S. Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy- derivatives. Bioorg. Med. Chem. Lett., 15(4), 873-876, 2005.
  • Rice, J.E., Cai, Z-W., He, Z-M., and LaVoie, E.J. Some observations on the palladium-catalyzed triflate-arene cyclization of electron-rich biaryl substrates.  J. Org. Chem., 60, 8101-8104, 1995.
  • He, Z-M., Weyand, E.H., Cai, Z-W., Wu, Y., Rice, J.E., and LaVoie, E.J.  11,12-Epoxy-9,10,11,12-tetrahydro-5,9,10-trihydroxybenzo[b]fluoranthene: Its role in the metabolic activation of B[b]F in mouse skin.  Polycyclic Aromatic Compounds, 6, 17-25, 1994.
  • Rice, J.E. and Cai, Z-W. An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes.  J. Org. Chem., 58, 1415-1424, 1993.
  • Weyand, E.H., Cai, Z-W., Wu, Y., Rice, J.E., He, Zhen-Min, and LaVoie, E.J. Detection of the major DNA adducts of benzo[b]fluoranthene on mouse skin:  Role of phenolic dihydrodiols.  Chem. Res. Toxicol., 6, 568-577, 1993.
  • Marshall, M.V., He, Z-M., Weyand, E.H., Rice, J.E., and LaVoie, E.J. Mutagenic activity of the 4,5- and 9,10-dihydrodiols of benzo[j]fluoranthene and their syn- and anti-dihydrodiol epoxides in Salmonella typhimurium.  Env. Mol. Mut., 22, 34-45, 1993.
  • Rice, J.E. and Cai, Z-W. A palladium-catalyzed intramolecular arene-triflate coupling for the synthesis of fluoranthenes and benzofluoranthenes.  Tetrahedron Letters, 33, 1675-1678, 1992.
  • He, Z-M. and Rice, J.E. Synthesis of anti- and syn-diol epoxides of trans-4,5-dihydro-4,5-dihydroxybenzo[j]­fluoranthene and trans-9,10-dihydro-9,10-dihydroxybenzo[j]fluoranthene.  J. Org. Chem., 57, 1784-1789, 1992.
  • Rice, J.E. and Beresis, R. A mild procedure for the preparation of phenols from polycyclic aromatic ketones. Polycyclic Aromatic Compounds, 2, 235-243, 1992.
  • Rice, J.E. and He, Z-M. Preparation of 4- and 10-fluorobenzo[j]fluoranthene via cyclodehydration of acetals and cyclopropyl carboxaldehydes. J. Org. Chem., 55, 5490-5494, 1990.
  • Rice, J.E., Weyand, E.H., Burrill, C., and LaVoie, E.J. Fluorine probes for investigating the mechanism of activation of indeno[1,2,3-cd]pyrene to a tumorigenic agent. Carcinogenesis, 11, 1971-1974, 1990.
  • Rice, J.E., Czech, A., Hussain, N., and LaVoie, E.J. Synthesis of fluorinated derivatives of benzo[k]fluoranthene and indeno[1,2,3-cd]pyrene and 8,9-dihydro-8,9-epoxy-benzo[k]fluoranthene.J.Org.Chem., 53,1775-1779, 1988.
  • Weyand, E.H., Geddie, N.G., Rice, J.E., Czech, A., Amin, S., and LaVoie, E.J. Metabolism and mutagenic activity of benzo[k]fluoranthene and 3-, 8-, and 9-fluorobenzo[k]fluor­anthene. Carcinogenesis, 9, 1277-1281, 1988.
  • Rice, J.E., Jordan, K., Little, P., Leon, A., and Hussain, N. Comparative tumor-initiating activity of methylene-bridged and bay region methylated derivatives of benz[a]anthracene and chrysene. Carcinogenesis, 9, 2275-2278, 1988.
  • Rice, J.E., DeFloria, M.C. Sensenhauser, Carlo, and LaVoie, E.J. The influence of fluoranthene on the metabolism and DNA binding of benzo[a]pyrene in vivo in mouse skin. Chem.-Biol. Interact., 68, 127-136, 1988.
  • Rice, J.E., Weyand, E.H., Geddie, N.G., DeFloria, M.C., and LaVoie, E.J. Identification of tumorigenic metabolites of benzo[j]fluoranthene formed in vivo in mouse skin. Cancer Res., 47, 6166-6170, 1987.
  • Rice, J.E., Rivenson, A., Braley, J. and LaVoie, E.J. Methylated derivatives of pyrene and fluorene: evaluation of genotoxicity in the hepatocyte/DNA repair test and tumorigenic activity in newborn mice. J. Toxicol. Environ. Health, 21, 525-532, 1987.
  • Rice, J.E., Hussain, N. and LaVoie, E.J. Synthesis of [ Methoxy -14C]Eugenol. J. Labelled Compd. Radiopharm., 24, 1043-1049, 1987.
  • Rice, J.E., Geddie, N.G. and LaVoie, E.J. Identification of metabolites of benzo[j]fluoranthene formed in vitro in rat liver homogenate. Chem.-Biol Interact., 63, 227-237, 1987.
  • Rice, J.E., Shih, H.C., Hussain, N. and LaVoie, E.J. Synthesis of the major metabolic dihydrodiols of benzo[j]fluoranthene. J. Org. Chem., 52, 849-855, 1987.
  • LaVoie, E.J., Braley, J., Rice, J.E. and Rivenson, A. Tumorigenic activity of nonalternant polynuclear aromatic hydro­carbons in newborn mice. Cancer Lett., 34, 15-20, 1987.
  • Weyand, E.H., Rice, J.E., and LaVoie, E.J. 32P-Postlabeling of DNA adducts from nonalternant PAH using thin-layer and high performance liquid chromatography. Cancer Lett., 37, 257-266, 1987.
  • Rice, J.E., LaVoie, E.J. McCaustland, D.J., Fischer, D.L. and Wiley, J.C. Synthesis of oxygenated metabolites of indeno(1,2,3-cd)­pyrene. J. Org. Chem., 51, 2428-2434, 1986.
  • Rice, J.E., Hosted, T.J., DeFloria, M.C., LaVoie, E.J., Fischer, D.L. and Wiley, J.C. Tumor-initiating activity of major in vivo metabolites of indeno[1,2,3-cd]pyrene on mouse skin. Carcinogenesis,7, 1761-1764, 1986.
  • LaVoie, E.J., Coleman, D.T., Rice, J.E., Geddie, N.G. and Hoffmann, D. Tumor-initiating activity, mutagenicity and metab­olism of methylated anthracenes. Carcinogenesis , 6, 1483-1488, 1985.
  • LaVoie, E.J., Coleman, D.T., Geddie, N.G. and Rice, J.E. Studies on the mutagenicity and tumor-initiating activity of methylated fluorenes. Chem.-Biol. Interactions, 52, 301-309, 1985.
  • Rice, J.E., Coleman, D.T., Hosted, T.J., LaVoie, E.J., McCaustland, D.J. and Wiley, J.C. Identification of mutagenic metabolites of indeno(1,2,3-cd)pyrene formed in vitro with rat liver enzymes. Cancer Res., 45, 5421-5425, 1985.
  • Rice, J.E., Makowski, G.S., Hosted, T.J. and LaVoie, E.J. Methylene-bridged bay region chrysene and phenanthrene deriva­tives and their keto-analogs: mutagenicity in S. typhimurium and tumor-initiating activity on mouse skin. Cancer Lett., 27, 199-206, 1985.
  • Rice, J.E., Hosted, T.J. and LaVoie, E.J. Fluoranthene and pyrene enhance BaP-DNA adduct formation in vivo in mouse skin. Cancer Lett., 24, 327-333, 1984.
  • Rice, J.E., LaVoie, E.J. and Hoffmann, D. Synthesis of the isomeric phenols and trans-2,3-dihydrodiol of fluoranthene. J. Org. Chem., 48, 2360-2363, 1983.
  • Rice, J.E., Wojciechowski, P.S. and Okamoto, Y.  A novel method for the synthesis of substituted tetrathia, diselenadithia, and tetraselenafulvalenes.  Heterocycles 18,191-199, 1982.
  • Rice, J.E. and Okamoto, Y.  Hydroboration of sterically hindered olefins under high pressure.  J. Org. Chem. 47,4189, 1982.
  • Rice, J.E. and Okamoto, Y.  One-step synthesis of substituted tetrathiafulvalenes under high pressure.  J. Org. Chem. 46, 446, 1981.

 

Teaching

Undergraduate

Graduate