- Imidazoline derivatives as alpha-1A adrenoceptor ligands
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Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
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Page/Page column 13
(2010/02/11)
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- 2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues
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A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.
- Hodson, Stephen J.,Bishop, Michael J.,Speake, Jason D.,Navas III, Frank,Garrison, Deanna T.,Bigham, Eric C.,Saussy Jr., David L.,Liacos, James A.,Irving, Paul E.,Jeffrey Gobel,Sherman, Bryan W.
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p. 2229 - 2239
(2007/10/03)
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- 149. Notizen zur Synthese von 2-Aminophenylsulfonen
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Syntheses of the alkyl, cycloalkyl and aryl 2-aminophenyl sulfones 10 were achieved by oxidation of the corresponding 2-nitrophenyl sulfides 7 to the 2-nitrophenyl sulfones 9 followed by ethanolic Bechamp-reduction.The sulfides 7 in turn were obtained by either reactions of 2-nitro-thiophenol (8) with the appropriate alkyl and cycloalkyl halides or of 2-chloro-nitrobenzene (5) with the relevant thiols.Condensation of 2-nitrobenzenesulfinic acid (3) with bromoacetic acid in aqueous alkaline solution led - presumably via 2-nitrophenylsulfonylacetic acid (4) - to methyl2-nitrophenyl sulfone (1), reduction of which gave 2-aminophenyl methyl sulfone (2).Treatment of 2-aminothiophenol (11) with t-butyl alcohol in aqueous sulfuric acid gave 2-aminophenyl t-butyl sulfide (12), which was acetylated to o-t-butylthio-acetanilide (13).Oxidation of the latter to o-t-butylsulfonyl-acetanilide (14) followed by hydrolysis led to 2-aminophenyl t-butyl sulfone (15).
- Courtin, Alfred,Tobel, Hans-Rudolf von,Auerbach, Guenther
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p. 1412 - 1419
(2007/10/02)
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