100837-08-9Relevant academic research and scientific papers
Synthesis and pharmacology of the putative novel muscarinic agonist (S)- 4-F-MePyMcN [(S)-4-(pyrrolidino)-1-methyl-2-butynyl-N-(4-fluorophenyl) carbamate oxalate]
Athmani, Saleh,Bradley, Karen N.,Harvey, Alan L.,Kornisiuk, Edgar,Jerusalinsky, Diana
, p. 935 - 941 (2007/10/03)
(S)-4-F-MePyMcN [(S)-4-(pyrrolidino)-1-methyl-2-butynyl-N-(4- fluorophenyl) carbamate oxalate] has been suggested to be a selective agonist at the M1 subtype of muscarinic receptor [Lambrecht G. et al., Life Sci. 56 (1995) 815-822]. We synthesized the compound and tested its selectivity for different muscarinic receptors with binding experiments using rat cerebral cortex synaptosomal membranes and cloned human ml to m5 receptors and by functional experiments on rabbit vas deferens preparations. There was little difference in affinity for the compound at the different cloned muscarinic receptors (IC50s for displacement of 3H-N-methylscopolamine were 0.7-1.0 μM). On rabbit vas deferens preparations, (S)-4-F-MePyMcN did reduce twitch responses to electrical stimulation like the known M1 agonist McN-A-343, but unlike McN-A-343 the compound reduced postsynaptic sensitivity to noradrenaline, ATP and KCl. Because of these additional actions, (S)-4-F- MePyMcN may not be suitable as a tool to study M1 muscarinic receptors selectively.
Pigments of Fungi. Part 38. Synthesis of Austrocorticinic Acid and (S)-(-)-Austrocorticin; Absolute Stereochemistry of Natural Austrocorticin
Cotterill, Ann S.,Gill, Melvyn,Gimenez, Alberto,Milanovic Nives M.
, p. 3269 - 3276 (2007/10/02)
The absolute configuration of the fungal anthraquinone (+)-austrocorticin 1 is established as (R) by synthesis of its antipode from (S)-(-)-but-3-yn-2-ol via a Diels-Alder reaction involving the highly functionalised, chiral butadiene 6.Similarly, austrocorticinic acid is made available from but-1-yne.
Stereoisomers of Allenic Amines as Inactivators of Monoamine Oxidase Type B. Stereochemical Probes of the Active Site
Smith, Roger A.,White, Robert L.,Krantz, Allen
, p. 1558 - 1566 (2007/10/02)
The kinetics of inactivation of mitochondrial monoamine oxidase type B (MAO-B) by a series of 18 stereoisomers of tertiary α-allenic amines have been investigated in detail.The chirality of the allene group in N-methyl-N-aralkylpenta-2,3-dienamines was found to have a profound effect on the inactivation rate, with the (R)-allenes being up to 200-fold more potent than their (S)-allenic counterparts.The ability of (S)-allenes to inactivate MAO was severely compromised by the presence of N-phenethyl or N-α-substituted-aralkyl substituents.The opposing chiralities in both the allene and aralkyl groups of (R,R)- and (S,S)-N-methyl-N-(1,2,3,4-tetrahydro-1-naphthyl)-penta-2,3-dieneamine resulted in a difference of more than 3 oredrs of magnitude in inactivation rates.The stereoselectivity of MAO-B was examined further with a series of reversible aralkylamine inhibitors; thus (R)-1,2,3,4-tetrahydro-1-naphthylamine was determined to be 150-fold more potent than its enantiomer.
