Sulfinalol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Sulfinalol
Sulfinalol.svg
Names
IUPAC name
4-[1-Hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]-2-methylsulfinylphenol
Identifiers
66264-77-5
Jmol 3D model Interactive image
PubChem 44439
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

Sulfinalol is a beta adrenergic receptor antagonist.[1]

Synthesis[edit]

The methyl group on a sulfoxide interestingly proves 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 reaagent such as metaperiodate gives sulfinalol (5).

References[edit]

  1. ^ "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.