New quinoline derivatives as nicotinic receptor modulators was written by Manetti, Dina;Bellucci, Cristina;Dei, Silvia;Teodori, Elisabetta;Varani, Katia;Spirova, Ekaterina;Kudryavtsev, Denis;Shelukhina, Irina;Tsetlin, Victor;Romanelli, Maria Novella. And the article was included in European Journal of Medicinal Chemistry in 2016.COA of Formula: C7H16Cl2N2 This article mentions the following:
As a continuation of previous work on quinoline derivatives, which showed some preference (2-3 times) for the 伪7 with respect to 伪4尾2 acetylcholine nicotinic receptors (nAChRs),the authors synthesized a series of novel azabicyclic or diazabicyclic compounds carrying a quinoline or isoquinoline ring, with the aim of searching for more selective 伪7 nAChR compounds Radioligand binding studies on 伪7* and 伪4尾2* nAChRs (rat brain homogenate) revealed one compound with a 2-fold higher affinity for the 伪4尾2*-subtype, and four compounds with at least 3-fold higher affinity for 伪7* nAChR. The most promising compound showed a Ki鈭?00 nM and over 10-fold selectivity for 伪7* nAChR. Other compounds at 50 渭M suppressed ion currents induced in the rat 伪4尾2 nAChR and the chimeric nAChR composed of the ligand-binding domain of the chick 伪7 and transmembrane domain of the 伪1 glycine receptor, expressed in Xenopus oocytes. Calcium imaging experiments on the human 伪7 nAChR expressed in the Neuro2a cells and potentiated by PNU-120596 confirmed the antagonistic activity for one compound and on the contrary other compounds were agonists with the EC50 values in the range of 1.0-1.6 渭M. Thus, the introduced modifications allowed us to enhance the selectivity of quinolines towards 伪7 nAChR and to get novel compounds with agonistic activity. The synthesis of the target compounds was achieved by a reaction of 1,4-diazabicyclo[3.2.2]nonane, 1,4-diazabicyclo[3.2.1]octane dihydrochloride, 1-Azabicyclo[2.2.2]octan-3-amine, hydrochloride (1:2) with (bromo)quinoline derivatives, quinolinecarboxylic acid derivatives, isoquinolinecarboxylic acid derivatives The title compounds thus formed included . In the experiment, the researchers used many compounds, for example, 3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2COA of Formula: C7H16Cl2N2).
3-Aminoquinuclidine dihydrochloride (cas: 6530-09-2) belongs to quinuclidine derivatives. Quinuclidine derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita鈥揃aylis鈥揌illman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).COA of Formula: C7H16Cl2N2
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider