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Stephen C Bergmeier - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of 5 substituted ring e analogs of Methyllycaconitine via the suzuki miyaura cross coupling reaction
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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The synthesis of 5-substituted ring E analogs of Methyllycaconitine via the Suzuki–Miyaura cross-coupling reaction
Bioorganic & medicinal chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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structure activity studies of ring e analogues of Methyllycaconitine part 2 synthesis of antagonists to the α3β4 nicotinic acetylcholine receptors through modifications to the ester
Bioorganic & Medicinal Chemistry Letters, 2004Co-Authors: Stephen C Bergmeier, Darrell L. Bryant, K. A. Ismail, Kristjan M. Arason, Susan B. Mckay, Dennis B. MckayAbstract:Abstract The development of novel agents for the differentiation of neuronal nicotinic acetylcholine receptors (nAChRs) is important for the treatment of a variety of pathological conditions. We have prepared and evaluated a number of simpler analogues of the norditerpeniod alkaloid Methyllycaconitine (MLA) in an effort to understand molecular determinants of nAChR•small molecule interactions. We have previously reported the synthesis and evaluation of a series of ring E analogues of MLA. We report here the optimization of the α3β4* functional activity of this series of compounds through modification of the ester.
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Effects of Methyllycaconitine and Related Analogues on Bovine Adrenal α3β4* Nicotinic Acetylcholine Receptors
Annals of the New York Academy of Sciences, 2002Co-Authors: Darrell L. Bryant, David J Lapinsky, Stephen C Bergmeier, R. Benjamin Free, Sara M Thomasy, K. A. Ismail, Kristjan M. Arason, Dennis B. MckayAbstract:Adrenal secretion and binding studies were performed using ring E analogues of Methyllycaconitine to assess structural determinants affecting activity on bovine adrenal alpha3beta4* nicotinic receptors. The most potent analogues are as potent as many inhibitors of adrenal secretion. Our data support the potential use of Methyllycaconitine analogues to generate nicotinic receptor subtype-specific compounds.
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ring e analogs of Methyllycaconitine mla as novel nicotinic antagonists
Bioorganic & Medicinal Chemistry Letters, 1999Co-Authors: Stephen C Bergmeier, David J Lapinsky, Benjamin R Free, Dennis B. MckayAbstract:We have prepared ring E analogs of the diterpenoid alkaloid Methyllycaconitine. These compounds have been assayed for nicotinic activity and were found to act as functional antagonists on adrenal nicotinic receptors.
Dennis B. Mckay - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of 5 substituted ring e analogs of Methyllycaconitine via the suzuki miyaura cross coupling reaction
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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The synthesis of 5-substituted ring E analogs of Methyllycaconitine via the Suzuki–Miyaura cross-coupling reaction
Bioorganic & medicinal chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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structure activity studies of ring e analogues of Methyllycaconitine part 2 synthesis of antagonists to the α3β4 nicotinic acetylcholine receptors through modifications to the ester
Bioorganic & Medicinal Chemistry Letters, 2004Co-Authors: Stephen C Bergmeier, Darrell L. Bryant, K. A. Ismail, Kristjan M. Arason, Susan B. Mckay, Dennis B. MckayAbstract:Abstract The development of novel agents for the differentiation of neuronal nicotinic acetylcholine receptors (nAChRs) is important for the treatment of a variety of pathological conditions. We have prepared and evaluated a number of simpler analogues of the norditerpeniod alkaloid Methyllycaconitine (MLA) in an effort to understand molecular determinants of nAChR•small molecule interactions. We have previously reported the synthesis and evaluation of a series of ring E analogues of MLA. We report here the optimization of the α3β4* functional activity of this series of compounds through modification of the ester.
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Effects of Methyllycaconitine and Related Analogues on Bovine Adrenal α3β4* Nicotinic Acetylcholine Receptors
Annals of the New York Academy of Sciences, 2002Co-Authors: Darrell L. Bryant, David J Lapinsky, Stephen C Bergmeier, R. Benjamin Free, Sara M Thomasy, K. A. Ismail, Kristjan M. Arason, Dennis B. MckayAbstract:Adrenal secretion and binding studies were performed using ring E analogues of Methyllycaconitine to assess structural determinants affecting activity on bovine adrenal alpha3beta4* nicotinic receptors. The most potent analogues are as potent as many inhibitors of adrenal secretion. Our data support the potential use of Methyllycaconitine analogues to generate nicotinic receptor subtype-specific compounds.
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ring e analogs of Methyllycaconitine mla as novel nicotinic antagonists
Bioorganic & Medicinal Chemistry Letters, 1999Co-Authors: Stephen C Bergmeier, David J Lapinsky, Benjamin R Free, Dennis B. MckayAbstract:We have prepared ring E analogs of the diterpenoid alkaloid Methyllycaconitine. These compounds have been assayed for nicotinic activity and were found to act as functional antagonists on adrenal nicotinic receptors.
Margaret A. Brimble - One of the best experts on this subject based on the ideXlab platform.
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Enantioselective synthesis of BE ring analogues of Methyllycaconitine
Tetrahedron, 2016Co-Authors: Emma Dickson, Margaret A. Brimble, Lisa I. Pilkington, David BarkerAbstract:Abstract The enantioselective synthesis of decahydroquinolines mimicking the BE rings of Methyllycaconitine (MLA) is reported. The analogues were synthesised via a one-pot cyclisation using ethyl α-(bromomethyl)acrylate, (R)-1-phenylethanamine and cyclohexanone to form chiral octahydroquinolines which can be selectively hydrogenated to form the 3-substituted-decahydroquinolines with the same stereochemistry found in MLA. The amine and ketone components in the one-pot reaction can also be altered to provide access to structurally related heterocycles.
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a double mannich approach to the synthesis of substituted piperidones application to the synthesis of substituted e ring analogues of Methyllycaconitine
ChemInform, 2011Co-Authors: Yinman Chan, Margaret A. Brimble, Jared Balle, Peter D. W. Boyd, Kevin J Sparrow, David BarkerAbstract:A set of E-ring analogues (X) of the delphinium alkaloid Methyllycaconitine (XI) is prepared from title compounds (VII) using established transformations.
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The enantioselective synthesis of tetracyclic Methyllycaconitine analogues
Tetrahedron, 2011Co-Authors: Kevin Sparrow, David Barker, Margaret A. BrimbleAbstract:Abstract A new enantioselective synthesis of ABEF ring analogues of Methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels–Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.
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A Double Mannich Approach to the Synthesis of Substituted Piperidones—Application to the Synthesis of Substituted E-Ring Analogues of Methyllycaconitine.
ChemInform, 2010Co-Authors: Yinman Chan, Margaret A. Brimble, Jared Balle, J. Kevin Sparrow, Peter D. W. Boyd, David BarkerAbstract:A set of E-ring analogues (X) of the delphinium alkaloid Methyllycaconitine (XI) is prepared from title compounds (VII) using established transformations.
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Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine
European Journal of Organic Chemistry, 2009Co-Authors: Holger Guthmann, Emma Wright, Daniel Conole, Karsten Körber, David Barker, Margaret A. BrimbleAbstract:The synthesis of AE and BE analogues of the alkaloid Methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2-(2-methylmaleimido)benzoate ester and a homocholine motif formed from a tertiary N-(3-phenylpropyl)amine incorporated into either a 3-azabicyclo[3.3.1]nonane (AE) or octahydroquinoline (BE) ring system. An additional aromatic group is introduced into the AE bicyclic system using a Horner–Wadsworth–Emmons reaction. The BE analogues are synthesised by a one-pot cyclisation using ethyl α-(bromomethyl)acrylate, a primary amine and cyclohexanone leading to an efficient assembly of an octahydroquinoline ring system that mimics the BE-rings of Methyllycaconitine. In both the AE and BE analogues, the key 2-(2-methylsuccinimido)benzoate ester pharmacophore is introduced by esterification of the alcohol precursors with 2-(2-methylmaleimido)benzoic acid (10) under Steglich conditions followed by hydrogenation over palladium on charcoal.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
David Barker - One of the best experts on this subject based on the ideXlab platform.
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Enantioselective synthesis of BE ring analogues of Methyllycaconitine
Tetrahedron, 2016Co-Authors: Emma Dickson, Margaret A. Brimble, Lisa I. Pilkington, David BarkerAbstract:Abstract The enantioselective synthesis of decahydroquinolines mimicking the BE rings of Methyllycaconitine (MLA) is reported. The analogues were synthesised via a one-pot cyclisation using ethyl α-(bromomethyl)acrylate, (R)-1-phenylethanamine and cyclohexanone to form chiral octahydroquinolines which can be selectively hydrogenated to form the 3-substituted-decahydroquinolines with the same stereochemistry found in MLA. The amine and ketone components in the one-pot reaction can also be altered to provide access to structurally related heterocycles.
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a double mannich approach to the synthesis of substituted piperidones application to the synthesis of substituted e ring analogues of Methyllycaconitine
ChemInform, 2011Co-Authors: Yinman Chan, Margaret A. Brimble, Jared Balle, Peter D. W. Boyd, Kevin J Sparrow, David BarkerAbstract:A set of E-ring analogues (X) of the delphinium alkaloid Methyllycaconitine (XI) is prepared from title compounds (VII) using established transformations.
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The enantioselective synthesis of tetracyclic Methyllycaconitine analogues
Tetrahedron, 2011Co-Authors: Kevin Sparrow, David Barker, Margaret A. BrimbleAbstract:Abstract A new enantioselective synthesis of ABEF ring analogues of Methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels–Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.
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A Double Mannich Approach to the Synthesis of Substituted Piperidones—Application to the Synthesis of Substituted E-Ring Analogues of Methyllycaconitine.
ChemInform, 2010Co-Authors: Yinman Chan, Margaret A. Brimble, Jared Balle, J. Kevin Sparrow, Peter D. W. Boyd, David BarkerAbstract:A set of E-ring analogues (X) of the delphinium alkaloid Methyllycaconitine (XI) is prepared from title compounds (VII) using established transformations.
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Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine
European Journal of Organic Chemistry, 2009Co-Authors: Holger Guthmann, Emma Wright, Daniel Conole, Karsten Körber, David Barker, Margaret A. BrimbleAbstract:The synthesis of AE and BE analogues of the alkaloid Methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2-(2-methylmaleimido)benzoate ester and a homocholine motif formed from a tertiary N-(3-phenylpropyl)amine incorporated into either a 3-azabicyclo[3.3.1]nonane (AE) or octahydroquinoline (BE) ring system. An additional aromatic group is introduced into the AE bicyclic system using a Horner–Wadsworth–Emmons reaction. The BE analogues are synthesised by a one-pot cyclisation using ethyl α-(bromomethyl)acrylate, a primary amine and cyclohexanone leading to an efficient assembly of an octahydroquinoline ring system that mimics the BE-rings of Methyllycaconitine. In both the AE and BE analogues, the key 2-(2-methylsuccinimido)benzoate ester pharmacophore is introduced by esterification of the alcohol precursors with 2-(2-methylmaleimido)benzoic acid (10) under Steglich conditions followed by hydrogenation over palladium on charcoal.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Susan B. Mckay - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of 5 substituted ring e analogs of Methyllycaconitine via the suzuki miyaura cross coupling reaction
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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The synthesis of 5-substituted ring E analogs of Methyllycaconitine via the Suzuki–Miyaura cross-coupling reaction
Bioorganic & medicinal chemistry, 2008Co-Authors: Junfeng Huang, Dennis B. Mckay, Crina M. Orac, Susan B. Mckay, Stephen C BergmeierAbstract:Abstract Novel 3,5-disubstituted ring E analogs of Methyllycaconitine were prepared and evaluated in nicotinic acetylcholine receptor binding assays. The desired analogs were prepared through the Suzuki–Miyaura cross-coupling reaction of methyl 5-bromo-nicotinate. The Suzuki–Miyaura cross-coupling reactions of pyridines with electron withdrawing substituents have not been extensively described previously.
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structure activity studies of ring e analogues of Methyllycaconitine part 2 synthesis of antagonists to the α3β4 nicotinic acetylcholine receptors through modifications to the ester
Bioorganic & Medicinal Chemistry Letters, 2004Co-Authors: Stephen C Bergmeier, Darrell L. Bryant, K. A. Ismail, Kristjan M. Arason, Susan B. Mckay, Dennis B. MckayAbstract:Abstract The development of novel agents for the differentiation of neuronal nicotinic acetylcholine receptors (nAChRs) is important for the treatment of a variety of pathological conditions. We have prepared and evaluated a number of simpler analogues of the norditerpeniod alkaloid Methyllycaconitine (MLA) in an effort to understand molecular determinants of nAChR•small molecule interactions. We have previously reported the synthesis and evaluation of a series of ring E analogues of MLA. We report here the optimization of the α3β4* functional activity of this series of compounds through modification of the ester.
