Quinuclidine, or 1-azabicyclo[2.2.2]octane, is an organic compound that belongs to the class of bridging ring amines. It is used as a catalyst and raw material for synthesis. It is strongly basic, with a conjugate acid pKa of 11.0. It can be obtained by the reduction of quinuclidine.
(J. Am. Chem. Soc. 2021, 143(11): 4133–4137.)
The study of quinuclidine and its derivative series can be traced back to the research of Professor M. V. Rubtsov in the USSR from 1940 to 1950. Representative features of quinine rings are bicyclic systems with bridgehead nitrogen atom, which possess high C3v symmetry and a rather rigid fixed structure. This unique structural feature gives the quinuclidine its unique properties. In contrast to the case of aliphatic, monocyclic and other 1-azabicyclic compounds, the conformational changes caused by the free rotation of atoms around the bond axis are essentially restricted in quinine rings. The rather strictly fixed structure of the quinuclidine bicyclic system leads not only to the disappearance of the free electron pair of the bridgehead nitrogen atom, but also to a well-defined spatial orientation along the axis of molecular symmetry.
The above-mentioned features of quinuclidine molecules offer a wide range of possibilities for the targeted search of new bioactive compounds. The rigid structure of the bicyclic system limits its conformational changes, making it possible to fix the distances between the reactive centers in the molecule and to exclude possible interactions between these centers, such as the formation of intramolecular hydrogen bonds and to suppress certain tautomeric transformations changing the reactivity of the compounds towards biochemical receptors. Some quinine ring derivatives prepared with the quinine ring as structural unit would have been modulators of nicotinic and/or this monoamine receptor, and said modulators can be used to treat diseases or disorders related to cholinergic receptors. In addition, it can also be used as M3 receptor antagonist and synthetase inhibitor.
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