Syntheses of (R)- and (S)-2- and 6-fluoronorepinephrine and (R)- and (S)-2- and 6-fluoroepinephrine: Effect of stereochemistry on fluorine-induced adrenergic selectivities

Journal of Medicinal Chemistry

Volumn 43, Issue 8, 2000, Pages 1611-1619

  Lu, Shou Fu ^a   Herbert, B ^a   Haufe, Günter ^b   Laue, Klaus Wilhelm ^b   Padgett, William L ^a   Oshunleti, O ^a   Daly, John W ^a   Kirk, Kenneth L ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENERGIC RECEPTOR STIMULATING AGENT; CATECHOLAMINE; FLUORONOEPINEPHRINE; NORADRENALIN; UNCLASSIFIED DRUG;

ADRENERGIC SYSTEM; ANIMAL TISSUE; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; FLUORINATION; ISOMERISM; NONHUMAN; RAT; REACTION ANALYSIS; RECEPTOR AFFINITY; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ADRENERGIC BETA-AGONISTS; ANIMALS; BINDING, COMPETITIVE; CEREBELLUM; CEREBRAL CORTEX; EPINEPHRINE; NOREPINEPHRINE; RADIOLIGAND ASSAY; RATS; RECEPTORS, ADRENERGIC, ALPHA-1; RECEPTORS, ADRENERGIC, ALPHA-2; RECEPTORS, ADRENERGIC, BETA-1; RECEPTORS, ADRENERGIC, BETA-2; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034692167     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990599h     Document Type: Article

References (21)

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2. (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991.
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21. In our previous work, racemic 2- and 6-fluoronorepinephrines and epinephrines were isolated consistently as the hemioxalates. In this study, we used NMR, HRMS, and chiral HPLC to confirm identity and purity, including enantio-purity, of the target compounds, initially assuming that the hemi-oxalates again would be obtained. However, comparison of apparent specific rotations of R- and S-1b, 1d, and 2d made it clear that R-1b, R-1d, and S-2d were present as the acid oxalates.