The Synthesis Of Nicotine Analogues

This research project focused on the designing and synthesis of nicotine analogues. Nicotine is a kind of alkaloid which was found in nightshade. It also presents in tobacco. Nicotine is a prototypical agonist of neuronal nicotinic acetylcholine receptors (nAChRs) and exerts an important modulatory influence on the CNS. Unfortunately, due to its actives against all subtypes of nAChRs, abuse of nicotine, toxic effects on the gastro intestinal and cardio vascular systems, it was prevented to be used as a drug for CNS disorders. This project was based on the computer-assisted drug designing method to design a series of nicotine analogues. The synthesis work started from aliphatic aldehydes. The pyridine ring was constructed by Vilsmeier reaction and pyrrolidine ring were formed using intramolecular hydroboration-cycloalkylation. Finally,22 nicotine analogues were synthesized. These analogues are being tested for their biological activities.