Preliminary Synthetic Studies of Methyllycaconitine, a Potent Nicotinic Acetylcholine Receptor Antagonist: Rapid Syntheses of AE-Bicyclic Analogues-Reference-Cited by-同舟云学术

Preliminary Synthetic Studies of Methyllycaconitine, a Potent Nicotinic Acetylcholine Receptor Antagonist: Rapid Syntheses of AE-Bicyclic Analogues

Published:1996-02 Issue:2 Volume:48 Page:210-213
ISSN:2042-7158
Container-title:Journal of Pharmacy and Pharmacology
language:en
Short-container-title:

Author:

Coates Philippa A¹,Blagbrough Ian S¹,Rowan Michael G¹,Pearson David P J²,Lewis Terence²,Potter Barry V L¹

Affiliation:

1. Department of Medicinal Chemistry, School of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath BA2 7AY

2. Zeneca Agrochemicals, Jealott's Hill Research Station, Bracknell RG12 6EY, UK

Abstract

Abstract A series of bicyclic analogues incorporating the homocholine motif of methyllycaconitine has been prepared to test the hypothesis that this is the essential pharmacophore of this potent, selective nicotinic receptor antagonist. A double Mannich reaction has been employed to construct the 3-azabicyclo[3.3.1]-nonane ring system, containing an N-ethylpiperidine moiety. The neopentyl-like alcohol was then esterified, using isatoic anhydride under basic conditions, to afford the corresponding anthranilate.

Publisher

Oxford University Press (OUP)

Subject

Pharmaceutical Science,Pharmacology

Link

http://academic.oup.com/jpp/article-pdf/48/2/210/37015272/j.2042-7158.1996.tb07125.x.pdf

Reference19 articles.

1. Synthesis of the A/E/F tricyclic section of the norditerpenoid alkaloid methyllycaconitine, a potent inhibitor of neurotransmission;Baillie;J. Chem. Soc., Chem. Commun.,1994

2. The toxicology and pharmacology of diterpenoid alkaloids;Benn,1983

3. Use of 2,6-disubstituted cyclohexanones and tropinone in the Mannich reaction;Blicke;J. Org. Chem.,1959

4. Rapid and efficient isolation of the nicotinic receptor antagonist methyllycaconitine from Delphinium: assignment of the methylsuccinimide absolute stereochemistry as S;Coates;Tetrahedron Letters,1994

5. Asymmetric total synthesis of atisine via intramolecular double Michael reaction;Ihara;J. Am. Chem. Soc.,1990

Cited by 21 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Formal Synthesis of Arboridinine Enabled by a Double-Mannich Reaction;The Journal of Organic Chemistry;2022-06-07

2. Expedient Construction of the ABEF Azatetracyclic Ring Systems of Lycoctonine-Type and 7,17-seco-Type C19-Diterpenoid Alkaloids;Organic Letters;2014-04-04

3. PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine;Tetrahedron;2013-07

4. Selective reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes;Russian Journal of Organic Chemistry;2011-06

5. Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine;European Journal of Organic Chemistry;2009-02-26