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Medroxalol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Medroxalol
Identifiers
  • 5-(2-{[4-(1,3-Benzodioxol-5-yl)-2-butanyl]amino}-1-hydroxyethyl)-2-hydroxybenzamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.054.618Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2O5
Molar mass372.421 g·mol−1
3D model (JSmol)
  • O=C(N)c1cc(ccc1O)C(O)CNC(C)CCc2ccc3OCOc3c2
  • 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

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

Synthesis

[edit]
Medroxalol synthesis:[2]

For the first step,salicylamide (1) is the subject of aFriedel-Crafts acetylation and then the aromaticmethyl ketone ishalogenated. in the usual manner. The bromide in2 is then displaced by the nitrogen inN-benzyl-1-(3',4'-methylenedioxyphenyl)-3-butylamine (3), which is itself prepared byreductive amination on the corresponding ketone. The product of the last step (4) iscatalytically 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

[edit]

References

[edit]
  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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