Stereochemical Studies on Medicinal Agents. IV.1 Conformational Analysis of Ephedrine Isomers and Related Compounds

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Abstract

The conformational preference of ephedrine isomers has been deduced from nmr studies of these compounds and the corresponding 3-methyl-2-phenylmorpholine diastereomers. The nmr data suggest that, in a variety of solvents, the ephedrines are intramolecularly hydrogen bonded both as the free bases and salts. A possible explanation for the stereo structure-activity relationship of the ephedrines has been advanced. Arylethanol-amines such as epinephrine and other related physiologically active compounds have been suggested to exist primarily as internally hydrogen-bonded species.

Original languageEnglish (US)
Pages (from-to)1057-1063
Number of pages7
JournalJournal of Medicinal Chemistry
Volume10
Issue number6
DOIs
StatePublished - Jan 1 1967

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Ephedrine
Hydrogen
Structure-Activity Relationship
Epinephrine
Amines
Salts

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abstract = "The conformational preference of ephedrine isomers has been deduced from nmr studies of these compounds and the corresponding 3-methyl-2-phenylmorpholine diastereomers. The nmr data suggest that, in a variety of solvents, the ephedrines are intramolecularly hydrogen bonded both as the free bases and salts. A possible explanation for the stereo structure-activity relationship of the ephedrines has been advanced. Arylethanol-amines such as epinephrine and other related physiologically active compounds have been suggested to exist primarily as internally hydrogen-bonded species.",
author = "Portoghese, {Philip S}",
year = "1967",
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journal = "Journal of Medicinal Chemistry",
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N2 - The conformational preference of ephedrine isomers has been deduced from nmr studies of these compounds and the corresponding 3-methyl-2-phenylmorpholine diastereomers. The nmr data suggest that, in a variety of solvents, the ephedrines are intramolecularly hydrogen bonded both as the free bases and salts. A possible explanation for the stereo structure-activity relationship of the ephedrines has been advanced. Arylethanol-amines such as epinephrine and other related physiologically active compounds have been suggested to exist primarily as internally hydrogen-bonded species.

AB - The conformational preference of ephedrine isomers has been deduced from nmr studies of these compounds and the corresponding 3-methyl-2-phenylmorpholine diastereomers. The nmr data suggest that, in a variety of solvents, the ephedrines are intramolecularly hydrogen bonded both as the free bases and salts. A possible explanation for the stereo structure-activity relationship of the ephedrines has been advanced. Arylethanol-amines such as epinephrine and other related physiologically active compounds have been suggested to exist primarily as internally hydrogen-bonded species.

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