Ring E analogs of methyllycaconitine (MLA) as novel nicotinic antagonists
Novel analogs of methyllycaconitine consisting of only ring E of MLA and the anthranoylsuccinimde side chain have been prepared. One of these analogs shows high affinity for the adrenal nicotinic receptor.
References (35)
- et al.
FEBS Lett.
(1988) - et al.
FEBS Lett.
(1990) - et al.
Tetrahedron Lett.
(1994) - et al.
Tetrahedron Lett.
(1998) - et al.
Tetrahedron Lett.
(1998) - et al.
Tetrahedron Lett.
(1998) - et al.
Tetrahedron Lett.
(1994) - et al.
J. Nat. Prod.
(1996) - et al.
J. Pharmacol. Exp. Ther.
(1984) Molec. Neurobiol.
(1997)
J. Med. Chem.
Ann. Rev. Physiol.
J. Neurosci.
Experentia
Experentia
Methods in Neurosciences
Can. J. Research
Cited by (51)
Small molecule ligands for α9 * and α7 nicotinic receptors: A survey and an update, respectively
2023, Pharmacological ResearchEnantioselective synthesis of BE ring analogues of methyllycaconitine
2016, TetrahedronCitation Excerpt :This reaction gave succinimido anthranilates 11a–h as 1:1 mixtures of diastereomers at the C-3″ position. Preparation of enantiopure succinimido anthranilates has previously been achieved via the three step process10q,16 however biological assessment has shown diastereomeric mixtures have similar activity to single isomers.9h,10l The decahydroquinoline BE rings of MLA 1 have an N-ethyl group and we envisaged that this could be introduced by hydrogenolysis of the (R)-α-methyl benzylamine moiety in 7c and subsequent addition of an ethyl moiety.
3D-QSAR and 3D-QSSR models of negative allosteric modulators facilitate the design of a novel selective antagonist of human α4β2 neuronal nicotinic acetylcholine receptors
2012, Bioorganic and Medicinal Chemistry LettersAconitum and Delphinium alkaloids of curare-like activity. QSAR analysis and molecular docking of alkaloids into AChBP
2010, European Journal of Medicinal ChemistryA double Mannich approach to the synthesis of substituted piperidones - Application to the synthesis of substituted E-ring analogues of methyllycaconitine
2010, TetrahedronCitation Excerpt :Functionalised piperidines and piperidones are also important intermediates in the synthesis of numerous other bioactive alkaloids and pharmaceuticals.7 There are few methods for the synthesis of 3,4,5-substituted piperidines,8 with many recent strategies for the synthesis of substituted piperidines aimed particularly at the synthesis of 2-substitued9 and 2,4- and 2,6-disubstitued10 piperidines. We herein report the synthesis of substituted E-ring analogues of methyllycaconitine beginning with a double Mannich reaction of acyclic β-keto esters to form the substituted piperidine ring.