Sulfinalol
Chemical compound
From Wikipedia, the free encyclopedia
Sulfinalol is a beta adrenergic receptor antagonist.[1]
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| Names | |
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| IUPAC name
4-[1-Hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]-2-methylsulfinylphenol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H27NO4S | |
| Molar mass | 377.50 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The preparation of sulfinalol begins by protection of the phenolic hydroxyl as its benzoate ester. Bromination followed by condensation with 4-(4-methoxyphenyl)butan-2-amine gives the amino ketone 3. Successive catalytic reduction and saponification affords amino alcohol 4. Oxidation of the sulfide to the sulfoxide with a reagent such as metaperiodate gives sulfinalol (5).
The methyl group on a sulfoxide is sufficiently acidic to substitute for phenolic hydroxyl.