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2153-98-2Relevant articles and documents
Stereochemical aspects of phenylethanolamine analogues as substrates of phenylethanolamine N-methyltransferase
Grunewald,Ye
, p. 1984 - 1986 (1988)
Phenylethylamines and phenylethanolamines represent two major classes of ligands for the epinephrine synthesizing enzyme, phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28). Phenylethylamines are usually competitive inhibitors and the isomers with the relative configuration as in (2S)-amphetamine and (2S)-2-aminotetralin are better inhibitors than their enantiomers. Phenylethanolamines are usually substrated of PNMT and the enzyme prefers the 1R isomers, such as (1R)-phenylethanolamine, in this class. Optically active norephedrines, norpseudoephedrines, and 2-amino-1-tetralols were used to study the stereochemical requirements of phenylethanolamines for PNMT active site binding. Although the norephedrines and the norpseudoephedrines were poorer ligands for PNMT than were the 2-amino-1-tetralols, (1R,2S)-(-)-norephedrine showed some activity as a pNMT substrate (K(m) = 1310 μM, V(max)/K(m) = 0.017). In the 2-amino-1-tetraols, the isomers with the 2S configuration showed higher affinity to PNMT (13, K(m) = 4.5 μM; 15, K(i) = 4.6 μM) and those with the 1R configuration were substrates for the PNMT-catalyzed methyl transfer (13, K(m) = 4.5 μM, V(max) = 0.16, 100 x V(max)/K(m) = 4.6; 16, K(m) = 195 μM, V(max) = 0.12, 100 x V(max)/K(m) = 0.062); the combination of 1R and 2S configurations, such as in (1R,2S)-2-amino-1-tetralol, was required for a good substrate. These stereochemical requirements derived from the norephedrines, the norpseudoephedrines, and the 2-amino-1-tetralols complement those for phenylethylamines and for phenylethanolamines and strongly suggest that phenylethylamine inhibitors bind to PNMT in the same orientation as do phenylethanolamine substrates.
Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases
Colman, Bob,De Sousa, Simon E.,O'Brien, Peter,Towers, Timothy D.,Watson, Will
, p. 4175 - 4182 (2007/10/03)
Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed.
STEREOCHEMICAL COURSE OF THE REACTION OF 2-HALOETHYL ISOTHIOCYANATES WITH NUCLEOPHILES. sTEREOSPECIFIC ROUTE TO 4,5-DISUBSTITUTED Δ2-THIAZOLINES AND THIAZOLIDINE-2-THIONES
Kniezo, Ladislav,Kristian, Pavol,Budesinsky, Milos,Havrilova, Katarina
, p. 717 - 728 (2007/10/02)
Diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes have been prepared.They reacted stereospecifically with CH3ONa, diethylamine, aniline and NaSH to give pure cis or trans-4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones whose configuration was determined using the nuclear Overhauser effect.The preponderant conformation of diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes was estimated on the basis of coupling constants of vicinal protons.