M E Kuehne

Summary

Affiliation: University of Vermont
Country: USA

Publications

  1. ncbi 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 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 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 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 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 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 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 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. ncbi 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 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
  • Christopher J Pace
  • Edinete M Silva
  • Jan Carlo Delorenzi
  • Wenjiang Zhang
  • Dumith Chequer Bou-Habib
  • Li-Wen He
  • Izabel C Frugulhetti
  • Elvira M Saraiva
  • Patrick A Jokiel
  • Claudio C Cirne-Santos
  • Edward M Sellers
  • Yamini Ramamoorthy
  • Leonardo Freire-de-Lima
  • Liwen He
  • Elvira M B Saraiva
  • Rachel F Tyndale
  • Cerli R Gattass
  • Deise de Andrade Costa

Detail Information

Publications11

  1. ncbi 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 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 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 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 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 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 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 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. ncbi 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 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 Anti-HIV-1 activity of the Iboga alkaloid congener 18-methoxycoronaridine
    Edinete M Silva
    , , 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...