Abstract
In the context of naturally occurring nitrogen heterocycles, nicotine is a chiral alkaloid present in tobacco plants, which can target and stimulate nicotinic acetylcholine receptors (nAChRs), a class of ligand-gated ion channels commonly located throughout the human brain. Due to its well-known toxicity for humans, there is considerable interest in the development of synthetic analogues; in particular, conformationally restricted analogues of nicotine have emerged as promising drug molecules for selective nAChR-targeting ligands. In the present mini-review, we will describe the synthesis of the conformationally restricted analogues of nicotine involving one or more catalytic processes. In particular, we will follow a systematic approach as a function of the heteroarene structure, considering: (a) 2,3-annulated tricyclic derivatives; (b) 3,4-annulated tricyclic derivatives; (c) tetracyclic derivatives; and (d) other polycyclic derivatives. For each of them we will also consider, when carried out, biological studies on their activity for specific nAChR subunits.
Highlights
The catalytic species involved in the synthetic pathway are indicated in blue
The catalytic species involved in the synthetic pathway are ind blue.Several studies have been performed on the nicotine derivative 4 in order to evaluate its biological activity
1996, a more i study by the same group showed an extensive examination of both enantiomers of the nicoextended study by the same group showed an extensive examination of both enantiomers tine analogue 15 in drug discrimination, discovering that neither generated nicotine-like of the nicotine analogue in drug discrimination, discovering that neither generated responses up to doses that suppress rate of responding; these results clearly demonstrated nicotine-like responses up to doses that suppress rate of responding; these results clearly for the first time that a potent antinociception can be produced with nicotine analogs that demonstrated for the first time that a potent antinociception can be produced with nicotine do not bind to nicotine receptors [46]
Summary
Well-known toxicity for humans, there is considerable interest in the dev Restricted Analogues of Nicotine alogues; in particular, conformationally restricted analogues of nicotine. Ing drug molecules for selective nAChR-targeting ligands. In the present m the synthesis of the conformationally restricted analogues of nicotine invo. Dipartimento di Chimica, Università degli Studi di Bari “Aldo Moro”, Via Edoardo Orabona 4, processes. (b) 3,4-annulated tricycl derivatives; and (d) other occurring polycyclic derivatives
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