Coaxing a Pyridine Nucleus To Give Up Its Aromaticity: Synthesis and Pharmacological Characterization of Novel Conformationally Restricted Analogues of Nicotine …

…, R Moaddel, R Yamaguchi, K Jozwiak…

Index: Sarkar, Tarun K.; Basak, Sankar; Wainer, Irving; Moaddel, Ruin; Yamaguchi, Rika; Jozwiak, Krzysztof; Chen, Hui-Ting; Lin, Chun-Cheng Journal of Medicinal Chemistry, 2004 , vol. 47, # 27 p. 6691 - 6701

Full Text: HTML

Citation Number: 15

Abstract

A series of novel nicotine and anabasine related conformationally restricted compounds including those with π-bonds in the connecting tether were synthesized following the hitherto unprecedented phenylsulfanyl group assisted generation of pyridine o- quinodimethane intermediates and their trapping by an intramolecular Diels-Alder reaction. Pharmacological characterization of some of these analogues at activating α3β4 nAChRs ...