The synthesis of 5-substituted ring E analogs of methyllycaconitine via the Suzuki-Miyaura cross-coupling reaction.
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.
Huang
Junfeng
J
Department of Chemistry and Biochemistry, Ohio University, Clippinger Laboratories, Athens, OH 45701, USA.
Orac
Crina M
CM
McKay
Susan
S
McKay
Dennis B
DB
Bergmeier
Stephen C
SC
D000157:Aconitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D011485:Protein Binding; D011950:Receptors, Cholinergic / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003432:Cross-Linking Reagents; D011950:Receptors, Cholinergic; C054634:methyllycaconitine; D000157:Aconitine