Medroxalol

Medroxalol is a vasodilator beta blocker also classified as a mixed receptor blocker as it blocks both alpha and beta receptors.[1]

Medroxalol
Identifiers
IUPAC name
  • 5-(2-{[4-(1,3-Benzodioxol-5-yl)-2-butanyl]amino}-1-hydroxyethyl)-2-hydroxybenzamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.054.618
Chemical and physical data
FormulaC20H24N2O5
Molar mass372.421 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N)c1cc(ccc1O)C(O)CNC(C)CCc2ccc3OCOc3c2
InChI
  • InChI=1S/C20H24N2O5/c1-12(2-3-13-4-7-18-19(8-13)27-11-26-18)22-10-17(24)14-5-6-16(23)15(9-14)20(21)25/h4-9,12,17,22-24H,2-3,10-11H2,1H3,(H2,21,25)
  • Key:MPQWSYJGFLADEW-UHFFFAOYSA-N

Synthesis
Medroxalol synthesis:[2]

For the first step, salicylamide (1) is the subject of a Friedel-Crafts acetylation and then the aromatic methylketone is halogenated. in the usual manner. The bromide in 2 is then displaced by the nitrogen in N-benzyl-1-(3',4'-methylenedioxyphenyl)-3-butylamine (3), which is itself prepared by reductive amination on the corresponding ketone. The product of the last step (4) is catalytically hydrogenated. This serves the dual purpose both of reducing the ketone and removing the benzyl protecting group affording the product medroxalol (5). Note that a benzyl protecting group is not necessarily used.

See also

References
  1. Dage RC, Cheng HC, Woodward JK (1981). "Cardiovascular properties of medroxalol, a new antihypertensive drug". Journal of Cardiovascular Pharmacology. 3 (2): 299–315. doi:10.1097/00005344-198103000-00009. PMID 6166802.
  2. J. T. Suh and T. M. Bare, U.S. Patent 3,883,560; Chem.Abstr. 83, 78914J (1975).


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