Medroxalol

Medroxalol
Identifiers
	IUPAC name 5-(2-{[4-(1,3-Benzodioxol-5-yl)-2-butanyl]amino}-1-hydroxyethyl)-2-hydroxybenzamide;
CAS Number	56290-94-9;
PubChem CID	41835;
ChemSpider	38173;
UNII	7PX96289JA;
CompTox Dashboard (EPA)	DTXSID30866550 ;
ECHA InfoCard	100.054.618
Chemical and physical data
Formula	C20H24N2O5
Molar mass	372.421 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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

Synthesis

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.

References

^ 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.
^ J. T. Suh and T. M. Bare, U.S. patent 3,883,560; Chem.Abstr. 83, 78914J (1975).

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[pmid6166802-1] 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).

[1]

[2]

Identifiers

IUPAC name 5-(2-{[4-(1,3-Benzodioxol-5-yl)-2-butanyl]amino}-1-hydroxyethyl)-2-hydroxybenzamide
CAS Number	56290-94-9
PubChem CID	41835
ChemSpider	38173
UNII	7PX96289JA
CompTox Dashboard (EPA)	DTXSID30866550
ECHA InfoCard	100.054.618
Chemical and physical data
Formula	C₂₀H₂₄N₂O₅
Molar mass	372.421 g·mol⁻¹
3D model (JSmol)	Interactive image
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

Medroxalol

Synthesis

See also

References

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