Synthesis of magnolol and its analogue compounds
AssigneesIndian Institute of Chemical Technology, Colgate-Palmolive Company
InventorsBasi V. Subba Reddy, Jhillu S. Yadav, Ravi Subramanyam
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Abstract
A method is described for producing magnolol, or a derivative or analogue thereof. The method includes obtaining MOM ether of 5,5′-diallylbiphenyl-2,2′-diol or a derivative or analogue thereof and subsequently converting the MOM ether of 5,5′-diallylbiphenyl-2,2′-diol into magnolol or a derivative or analogue thereof.
Claims22
A method of producing a compound of formula (I)
- wherein R represents H, alkyl, a substituted or unsubstituted phenyl;
- or a pharmaceutically or orally acceptable salt thereof, comprising
- (a) reacting a compound of formula (II);
- with bromine in an organic solvent to obtain a compound of formula (III);
- (b) reacting the compound of formula III with MOM-Cl in an organic solvent in the presence of an organic base to obtain a compound of formula (IV);
- (c) reacting the compound of formula IV with R—CH═CH—CH2—Br, wherein R is defined as above, in an organic solvent with magnesium and ethyl bromide to obtain a compound of formula V;
- (d) convening the compound of formula V with an suitable deprotecting agent in an organic solvent to obtain a compound of formula I;
- and
- (e) optionally, convening the compound of formula I to its pharmaceutically or orally acceptable salts.
A method of producing magnolol (5,5′-diallylbiphenyl-2,2′-diol) comprising:
- (a) reacting 2,2′-bisphenol with bromine in chloroform to obtain 5,5′-dibromo-2,2′-bisphenol;
- (b) reacting 5,5′-dibromo-2,2′-bisphenol with methoxymethylchloride (MOM-Cl) in dichloromethane with diisopropylethylamine to obtain MOM ether of 5,5′-dibromo-2,2′-bisphenol;
- (e) reacting the said MOM ether of 5,5′-dibromo-2,2′-bisphenol with allyl bromide in tetrahydrofuran with magnesium and ethyl bromide to obtain MOM ether of 5,5′-diallylbiphenyl-2,2′-diol;
- (d) converting the said MOM ether of 5,5′-diallylbiphenyl-2,2′-diol with a suitable deprotecting agent to obtain magnolol;
- and
- (e) optionally, converting magnolol to its pharmaceutically or orally acceptable salts.
A method of producing compound of formula V,
- comprising reacting a compound of formula IV
- with R—CH═CH—CH2—Br, wherein R represents H, alkyl, a substituted or unsubstituted phenyl, in an organic solvent for a sufficient amount of time to obtain a compound of formula V, and optionally converting the compound of formula V to a compound of formula I
A composition comprising an effective amount of magnolol prepared according to claim and an orally or pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.