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词条 Sulfinalol
释义

  1. Synthesis

  2. References

{{Chembox
| ImageFile = Sulfinalol.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = 4-[1-Hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]-2-methylsulfinylphenol
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 66264-77-5
| PubChem = 44439
| 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
| InChIKey= PAQZZCOZHPGCFW-UHFFFAOYSA-N
| ChemSpiderID =
| SMILES = CC(CCC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)S(=O)C)O}}
|Section2={{Chembox Properties
| C=20 | H=27 | N=1 | O=4 | S=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}Sulfinalol is a beta adrenergic receptor antagonist.[1]

Synthesis

The methyl group on a sulfoxide is sufficiently acidic to substitute for phenolic hydroxyl.

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. ^{{cite journal|pmid=6182405 | volume=4 | issue=5 | title=Studies on the mechanism of the acute antihypertensive and vasodilator actions of several beta-adrenoceptor antagonists | year=1982 | journal=J. Cardiovasc. Pharmacol. | pages=749–58}}
{{Adrenergics}}{{organic-compound-stub}}{{pharma-stub}}

3 : Beta blockers|Sulfoxides|Phenols

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