The synthesis of 5-substituted ring E analogs of methyllycaconitine via the Suzuki-Miyaura cross-coupling reaction

Junfeng Huang; Crina M Orac; Susan McKay; Dennis B McKay; Stephen C Bergmeier

doi:10.1016/j.bmc.2008.01.050

The synthesis of 5-substituted ring E analogs of methyllycaconitine via the Suzuki-Miyaura cross-coupling reaction

Bioorg Med Chem. 2008 Apr 1;16(7):3816-24. doi: 10.1016/j.bmc.2008.01.050. Epub 2008 Jan 31.

Authors

Junfeng Huang¹, Crina M Orac, Susan McKay, Dennis B McKay, Stephen C Bergmeier

Affiliation

¹ Department of Chemistry and Biochemistry, Ohio University, Clippinger Laboratories, Athens, OH 45701, USA.

PMID: 18272373
DOI: 10.1016/j.bmc.2008.01.050

Abstract

Novel 3,5-disubstituted ring E analogs of methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki-Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki-Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aconitine / analogs & derivatives*
Aconitine / chemical synthesis
Aconitine / chemistry
Cross-Linking Reagents / chemistry*
Hydrogenation
Molecular Structure
Protein Binding
Receptors, Cholinergic / metabolism
Stereoisomerism
Structure-Activity Relationship

Substances

Cross-Linking Reagents
Receptors, Cholinergic
methyllycaconitine
Aconitine

Grants and funding

DA13939/DA/NIDA NIH HHS/United States