M E Kuehne

Summary

Affiliation: University of Vermont
Country: USA

Publications

  1. ncbi request reprint Biogenetic syntheses of kopsijasminilam and deoxykopsijasminilam
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington 05405, USA
    J Org Chem 65:6434-40. 2000
  2. ncbi request reprint New ferrocenyl chiral auxiliary substituents for amines: applications to syntheses of mossambine and vinblastine
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
    J Org Chem 66:1560-6. 2001
  3. ncbi request reprint Syntheses of 5a'-homo-vinblastine and congeners designed to establish structural determinants for isolation of atropisomers
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, 05405, USA
    J Org Chem 66:5303-16. 2001
  4. ncbi request reprint The syntheses of 16a'-homo-leurosidine and 16a'-homo-vinblastine. Generation of atropisomers
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, 05405, USA
    J Org Chem 66:5317-28. 2001
  5. ncbi request reprint Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents
    Martin E Kuehne
    Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA
    J Med Chem 46:2716-30. 2003
  6. ncbi request reprint A biomimetic synthesis of the pauciflorine A and B skeleton
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington 05405, USA
    Org Lett 1:1749-50. 1999
  7. ncbi request reprint Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration
    Christopher J Pace
    Center for Neuropharmacology and Neuroscience, The Albany Medical College, MC 136, 47 New Scotland Avenue, Albany, NY 12208, USA
    Eur J Pharmacol 492:159-67. 2004
  8. ncbi request reprint Syntheses and biological evaluation of vinblastine congeners
    Martin E Kuehne
    Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
    Org Biomol Chem 1:2120-36. 2003
  9. pmc In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis
    Jan Carlo Delorenzi
    Departamento de Imunologia, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
    Antimicrob Agents Chemother 46:2111-5. 2002
  10. ncbi request reprint Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19
    Wenjiang Zhang
    Center for Addiction and Mental Health, University of Toronto, Toronto, Canada
    Drug Metab Dispos 30:663-9. 2002

Collaborators

  • Y L Li
  • F Xu
  • I M Maisonneuve
  • STANLEY GLICK
  • MARK FLECK
  • Edinete M Silva
  • Christopher J Pace
  • Wenjiang Zhang
  • Jan Carlo Delorenzi
  • Dumith Chequer Bou-Habib
  • Li Wen He
  • Elvira M Saraiva
  • Patrick A Jokiel
  • Claudio C Cirne-Santos
  • Bernardo Galvão-Castro
  • Izabel C Frugulhetti
  • Cerli R Gattass
  • Leonardo Freire-de-Lima
  • Elvira M B Saraiva
  • Edward M Sellers
  • Liwen He
  • Rachel F Tyndale
  • Deise de Andrade Costa
  • Yamini Ramamoorthy

Detail Information

Publications11

  1. ncbi request reprint Biogenetic syntheses of kopsijasminilam and deoxykopsijasminilam
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington 05405, USA
    J Org Chem 65:6434-40. 2000
    ..Formation of a carbamate, introduction of a second double bond at C-16, and conjugate reductive hydroxylation at C-20, or hydrogenation, gave the title products...
  2. ncbi request reprint New ferrocenyl chiral auxiliary substituents for amines: applications to syntheses of mossambine and vinblastine
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
    J Org Chem 66:1560-6. 2001
    ..Thus, key intermediates leading to mossambine and vinblastine could be synthesized with high enantioselectivity. The enantioselectivity greatly exceeds that found with other chiral N-auxiliaries developed in our studies...
  3. ncbi request reprint Syntheses of 5a'-homo-vinblastine and congeners designed to establish structural determinants for isolation of atropisomers
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, 05405, USA
    J Org Chem 66:5303-16. 2001
    ....
  4. ncbi request reprint The syntheses of 16a'-homo-leurosidine and 16a'-homo-vinblastine. Generation of atropisomers
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington, 05405, USA
    J Org Chem 66:5317-28. 2001
    ..The synthesis was achieved through a stereoselective inversion of the tertiary hydroxyl function in the enantioselectively generated C-20' progenitor 39...
  5. ncbi request reprint Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents
    Martin E Kuehne
    Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA
    J Med Chem 46:2716-30. 2003
    ..The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities...
  6. ncbi request reprint A biomimetic synthesis of the pauciflorine A and B skeleton
    M E Kuehne
    Department of Chemistry, University of Vermont, Burlington 05405, USA
    Org Lett 1:1749-50. 1999
    ..formula: see text] Racemic minovincine (3), following cyclization, reduction, O-tosylation, fragmentation, and carbamate formation, provided the deoxypauciflorine 12...
  7. ncbi request reprint Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration
    Christopher J Pace
    Center for Neuropharmacology and Neuroscience, The Albany Medical College, MC 136, 47 New Scotland Avenue, Albany, NY 12208, USA
    Eur J Pharmacol 492:159-67. 2004
    ..These compounds may constitute a new class of synthetic agents that act via the nicotinic alpha3beta4 mechanism to combat addiction...
  8. ncbi request reprint Syntheses and biological evaluation of vinblastine congeners
    Martin E Kuehne
    Department of Chemistry, University of Vermont, Burlington, VT 05405, USA
    Org Biomol Chem 1:2120-36. 2003
    ..An ID50 range of >10(7) M concentrations was found for L1210 inhibition by these compounds, with the most active 1000x as potent as vinblastine...
  9. pmc In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis
    Jan Carlo Delorenzi
    Departamento de Imunologia, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
    Antimicrob Agents Chemother 46:2111-5. 2002
    ..Despite their potent leishmanicide effect, both alkaloids were neither toxic to murine macrophages nor did they modulate their oxidative or cytokine production responses...
  10. ncbi request reprint Metabolism of 18-methoxycoronaridine, an ibogaine analog, to 18-hydroxycoronaridine by genetically variable CYP2C19
    Wenjiang Zhang
    Center for Addiction and Mental Health, University of Toronto, Toronto, Canada
    Drug Metab Dispos 30:663-9. 2002
    ..The apparent selectivity of this pathway for CYP2C19 suggests 18-MC as a potentially useful probe of CYP2C19 activity in vitro and in vivo...
  11. ncbi request reprint Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine
    Edinete M Silva
    Laboratório Avançado de Saúde Pública, Centro de Pesquisas Goncalo Moniz, Salvador, BA, Brazil
    Planta Med 70:808-12. 2004
    ..6 and 34.5. 18-MC moderately inhibits the HIV-1 enzyme reverse transcriptase (IC (50) = 69.4 microM), which at least partially explains its antiretroviral activity...