Sulfinalol

Sulfinalol

Names
IUPAC name 4-[1-Hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]-2-methylsulfinylphenol
Identifiers
CAS Number	66264-77-5
Jmol interactive 3D	Image
PubChem	44439
InChI InChI=1S/C20H27NO4S/c1-14(4-5-15-6-9-17(25-2)10-7-15)21-13-19(23)16-8-11-18(22)20(12-16)26(3)24/h6-12,14,19,21-23H,4-5,13H2,1-3H3 Key: PAQZZCOZHPGCFW-UHFFFAOYSA-N
SMILES CC(CCC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)S(=O)C)O
Properties
Chemical formula	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

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

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.