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Sulfinalol
Names
IUPAC name
4-[1-Hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]-2-methylsulfinylphenol
Identifiers
UNII
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
CC(CCC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)S(=O)C)O
Properties
C 20 H 27 N O 4 S
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).
Chemical compound
Sulfinalol is a
beta adrenergic receptor antagonist .
[1]
Synthesis
The methyl group on a sulfoxide is sufficiently acidic to substitute for phenolic hydroxyl.
Sulfinalol synthesis:
[2] R. E. Philion, (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 ).
References
^ Sybertz, E. J.; Baum, T.; Pula, K. K.; Nelson, S.; Eynon, E.; Sabin, C. (1982).
"Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists" . J. Cardiovasc. Pharmacol . 4 (5): 749–58.
doi :
10.1097/00005344-198209000-00009 .
PMID
6182405 .
S2CID
34100646 .
^
DE 2728641 , Philion, Richard Everett, "4-Hydroxyphenylalkanolaminderivate und Verfahren zu deren Herstellung [4-Hydroxyphenylalkanolamine derivatives and processes preparation thereof]", published 1978-01-05, assigned to
Sterling Drug Inc.
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