Literature DB >> 25941557

Tying up Nicotine: New Selective Competitive Antagonist of the Neuronal Nicotinic Acetylcholine Receptors.

Ida Nymann Petersen1, François Crestey1, Anders A Jensen1, Dinesh C Indurthi2, Henrik Pedersen3, Jesper T Andreasen1, Thomas Balle2, Jesper L Kristensen1.   

Abstract

Conformational restriction of the pyrrolidine nitrogen in nicotine by the introduction of an ethylene bridge provided a potent and selective antagonist of the α4β2-subtype of the nicotinic acetylcholine receptors. Resolution by chiral SFC, pharmacological characterization of the two enantiomers, and determination of absolute configuration via enantioselective synthesis showed that the pharmacological activity resided almost exclusively in the (R)-enantiomer.

Entities:  

Keywords:  Bridged-nicotine analogue; Negishi cross-coupling reaction; nAChRs; oocyte; selective antagonist

Year:  2015        PMID： 25941557      PMCID： PMC4416435          DOI： 10.1021/acsmedchemlett.5b00028

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  23 in total

Review 1.  Nicotinic acetylcholine receptors and depression: a review of the preclinical and clinical literature.

Authors:  Noah S Philip; Linda L Carpenter; Audrey R Tyrka; Lawrence H Price
Journal:  Psychopharmacology (Berl)       Date:  2010-07-08       Impact factor: 4.530

2.  Pharmacological investigation of (+)- and (-)-cis-2,3,3a,4,5,9b-hexahydro-1-methyl-1H-pyrrolo-[3,2-h]isoq uinoline, a bridged-nicotine analog.

Authors:  M I Damaj; W Glassco; M J Marks; B Slobe; J R James; E L May; J A Rosecrans; A C Collins; B R Martin
Journal:  J Pharmacol Exp Ther       Date:  1997-09       Impact factor: 4.030

3.  Unraveling the high- and low-sensitivity agonist responses of nicotinic acetylcholine receptors.

Authors:  Kasper Harpsøe; Philip K Ahring; Jeppe K Christensen; Marianne L Jensen; Dan Peters; Thomas Balle
Journal:  J Neurosci       Date:  2011-07-27       Impact factor: 6.167

4.  The characterization of a novel rigid nicotine analog with alpha7-selective nAChR agonist activity and modulation of agonist properties by boron inclusion.

Authors:  Roger L Papke; Guangrong Zheng; Nicole A Horenstein; Linda P Dwoskin; Peter A Crooks
Journal:  Bioorg Med Chem Lett       Date:  2005-09-01       Impact factor: 2.823

5.  A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex.

Authors:  J R Copeland; A Adem; P Jacob; A Nordberg
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1991-02       Impact factor: 3.000

6.  Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Authors:  Graeme Barker; Julia L McGrath; Artis Klapars; Darren Stead; George Zhou; Kevin R Campos; Peter O'Brien
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

7.  Complex-induced proximity effects: the effect of varying directing-group orientation on carbamate-directed lithiation reactions.

Authors:  K M Gross; P Beak
Journal:  J Am Chem Soc       Date:  2001-01-17       Impact factor: 15.419

8.  Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors:  Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419

9.  Synthesis, optical resolution, absolute configuration, and preliminary pharmacology of (+)- and (-)-cis-2,3,3a,4,5,9b-hexahydro-1-methyl-1H- pyrrolo-[3,2-h]isoquinoline, a structural analog of nicotine.

Authors:  W Glassco; J Suchocki; C George; B R Martin; E L May
Journal:  J Med Chem       Date:  1993-10-29       Impact factor: 7.446

Review 10.  Mammalian nicotinic acetylcholine receptors: from structure to function.

Authors:  Edson X Albuquerque; Edna F R Pereira; Manickavasagom Alkondon; Scott W Rogers
Journal:  Physiol Rev       Date:  2009-01       Impact factor: 37.312
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  1 in total

Review 1.  Synthetic Methods for the Preparation of Conformationally Restricted Analogues of Nicotine.

Authors:  Biswajit Panda; Gianluigi Albano
Journal:  Molecules       Date:  2021-12-13       Impact factor: 4.411
  1 in total

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