- Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists-Structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)
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Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the α4β2, α3β4, α4β4 and α7 neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the α3β4 nAChR.
- Hansen, Camilla P.,Jensen, Anders A.,Balle, Thomas,Bitsch-Jensen, Klaus,Hassan, Mohamud M.,Liljefors, Tommy,Frolund, Bente
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supporting information; experimental part
p. 87 - 91
(2009/09/25)
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- Reactions of phenyldimethylsilyllithium with β-N,N- dimethylaminoenones: A convenient synthesis of β-dimethyl(phenyl) silylacrylic acid and its derivatives
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Phenyldimethylsilyllithium reacted with 5,5-dimethyl-3-(N,N,-dimethylamino) cyclohex-2-enone (7), 3-(E)-N,N-dimethylaminopropenal (11), and 4-N,N-dimethylaminobut-3-en-2-one (13) to give the corresponding β-silyl-α,β-unsaturated carbonyl compounds 8, 12, and 14, in which the dimethylamino group has been displaced by the phenyldimethylsilyl group. Phenyldimethylsilyllithium reacted with ethyl β-N,N- dimethylaminopropenoate (15) by conjugate addition, but, in contrast to the ketones 7 and 13 and the aldehyde 11, the intermediate enolate 16 was C-protonated in the aqueous work-up to give ethyl 3-N,N-dimethylamino-3- dimethyl(phenyl)silylpropanoate (17). When the enolate 16 was instead given a mysteriously brief treatment with methyl iodide before work-up, the product was ethyl 3-(E)-dimethy(phenyl)silylpropenoate (18). Phenyllithium and methyllithium also added conjugatively to ethyl β-N,N-dimethylaminoacrylate (15) but, in contrast to the silyl case, the intermediate enolate 22 reacted unexceptionally with methyl iodide to give the products 25 and 26 of stereoselective C-methylation. This synthesis of the ester 18 was used to synthesize the Oppolzer sultam derivative 30.
- Fleming, Ian,Marangon, Elena,Roni, Chiara,Russell, Matthew G.,Chamudis, Sandra Taliansky
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p. 325 - 332
(2007/10/03)
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- Reactions of phenyldimethylsilyllithium with β-N,N-dimethylaminoenones
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Phenyldimethylsilyllithium reacts with the β-N,N-dimethylaminoenones 1 and 7, with the enal 5, and with ethyl β-N,N-dimethylaminoacrylate 9 to give the corresponding α,β-unsaturated carbonyl compounds with a β-phenyldimethylsilyl group, but in the last ca
- Fleming, Ian,Marangon, Elena,Roni, Chiara,Russell, Matthew G.,Chamudis, Sandra Taliansky
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p. 200 - 201
(2007/10/03)
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- Synthesis of 4-alkoxy and 3-nitro substituted isoxazolidines by catalyzed 1,3-dipolar cycloaddition reactions of nitrones with vinyl ethers and nitro alkenes
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1,3-Dipolar cycloadditions of the C-phenyl-N-alkylnitrones 1,3 and the C,N-diphenylnitrone (2) with vinyl ethers 5,6 are strongly catalyzed by chiral oxazaborolidines derived from N-arylsulfonyl substituted L-α-amino acids valine and tert-butyl leucine an
- Meske, Michael
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p. 426 - 433
(2007/10/03)
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- New synthesis of β-aminoacid derivatives via hydroamination in Dimcarb
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A new selective hydro-dimethylamination method for unsaturated carboxylic acid derivatives with the pronucleophilic dimethylamine-precursor Dimcarb is described, which allows effective synthesis of hydro-β-dimethylamino-acid derivatives and unsaturated amides. Simple HMO quantum chemical calculation together with 1H NMR examination permits the prediction of suitable substrates, coupling position for dimethylamine as well as for mechanistical insights and optimal reaction course.
- Hess,Dunkel,Muller
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p. 591 - 597
(2007/10/02)
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