Sulfinalol
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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PubChem CID |
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| UNII | |
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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). | |
| Infobox references | |
Synthesis
The methyl group on a sulfoxide is sufficiently acidic to substitute for phenolic hydroxyl.
Sulfinalol synthesis: R. E. Philion, DE 2728641 (1978 to Sterling), C.A. 90, 137468 (1979).
The preparation of this combined α- and β-blocker sulfinalol begins by protection of the phenolic hydroxyl as its benzoate ester. Bromination followed by condensation with 4-(4-methoxyphenyl)butan-2-amine (not PMA) gives the aminoketone 3. Successive catalytic reduction and saponification affords aminoalcohol 4. Oxidation of the sulfide to the sulfoxide with a reagent such as metaperiodate gives sulfinalol (5).
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gollark: My RPi runs Void, although who knows if it's actually on/working.
gollark: RASPBERRY PI OS POSSIBLY BAD?
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References
- "Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists". J. Cardiovasc. Pharmacol. 4 (5): 749–58. 1982. PMID 6182405.
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