The synthesis and nicotinic binding activity of (+/-)-epiquinamide and (+/-)-C(1)-epiepiquinamide.
The synthesis of (+/-)-epiquinamide 1 and (+/-)-C(1)-epiepiquinamide 2 based on the use of a Curtius rearrangement to introduce the C(1) amino residue is reported. In a competition binding assay for [(3)H]epibatidine binding to rat brain membranes neither (+/-)-1 nor (+/-)-2 showed any significant level of nicotinic activity.
Kanakubo
Akira
A
School of Chemistry, University of Bristol, UK.
Gray
Diane
D
Innocent
Neal
N
Wonnacott
Susan
S
Gallagher
Timothy
T
D000818:Animals; D001665:Binding Sites; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D009538:Nicotine / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats
D004952:Esters; D011807:Quinolizines; C481035:epiquinamide; D009538:Nicotine