3-amino-1-phenoxybutan-2-ols and 1-amino-3-phenoxybutan-2-ols as potentially active beta-adrenergic antagonists

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dc.contributor.advisorBoblitt, Robert L.
dc.contributor.committeeMemberLemke, Thomas L.
dc.contributor.committeeMemberEuler, Kenneth L.
dc.contributor.committeeMemberWillcott, Mark Robert, III
dc.creatorCapiton, George Adolphe
dc.date.accessioned2022-06-20T16:58:03Z
dc.date.available2022-06-20T16:58:03Z
dc.date.issued1974
dc.description.abstractTo study the relationship between side-chain methylation and selective beta-receptor antagonism, eight aminophenoxybutanols were prepared, comprised of two series containing four compounds each: (A) 3-amino-1-phenoxybutan-2-ols(I), and (B) l-amino-3-phenoxybutan-2-ols(II). Synthesis was achieved by treating two isomeric phenols (4,4-dimethylphenol or 4-ethylphenol) with 3-bromo-1,2-epoxybutane, catalyzed with BF[subscript 3]-etherate, which resulted in a mixture of 3-bromo-1-phenoxy- and 1-bromo-3-phenoxybutan-2-ols. Subsequent refluxing with i-propyl- or t-butylamine afforded I and II. The mixture thus formed was separated by column chromatography and found to consist of approximately 30% I and 70% II. The structure of II was unexpected; it was assumed that a 3-amino-2-phenoxybutan-l-ol (the "abnormal" product) would prevail. PMR, CMR and mass spectral data were employed for structure elucidation.
dc.description.departmentPharmacy, College of
dc.format.digitalOriginreformatted digital
dc.format.mimetypeapplication/pdf
dc.identifier.other13805680
dc.identifier.urihttps://hdl.handle.net/10657/9514
dc.language.isoen
dc.rightsThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. Section 107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.
dc.title3-amino-1-phenoxybutan-2-ols and 1-amino-3-phenoxybutan-2-ols as potentially active beta-adrenergic antagonists
dc.type.dcmiText
dc.type.genreThesis
thesis.degree.collegeCollege of Pharmacy
thesis.degree.departmentPharmacy, College of
thesis.degree.disciplinePharmacy
thesis.degree.grantorUniversity of Houston
thesis.degree.levelMasters
thesis.degree.nameMaster of Science

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