Flavonoid dimers and methods of making and using such

A method of synthesizing a compound of formula I:

• flavonoid-linker-flavonoid I
• wherein
• the flavonoid is apigenin;
• and
• the linker is a group having 3 or 4 ethylene glycol units;
• including the steps of:
• a) reacting p-hydroxybenzaldehyde with a compound of formula II to form a compound of formula III
• wherein R1 is selected from —H, -tosylate, and -mesylate;
• and
• b) reacting the compound of formula III with a compound of formula IV
• to form the compound of formula I, wherein R is selected from the group consisting of —H, benzyl, and methoxymethyl.

A method of synthesizing a compound of formula I:

• flavonoid-linker-flavonoid I
• wherein
• the flavonoid is apigenin;
• and
• the linker is a group having 3 or 4 ethylene glycol units;
• including the steps of:
• a) reacting p-hydroxybenzaldehyde with a compound of formula IV to form a compound of formula V
• wherein R is selected from the group consisting of —H, benzyl and methoxymethyl;
• and
• b) reacting the compound of formula V with a compound of formula II to form the compound of formula I
• wherein R1 is selected from —H, -tosylate, and -mesylate.

A method of reducing P-glycoprotein based multidrug resistance including the step of administering an effective amount of a compound of formula I:

• flavonoid-linker-flavonoid I
• wherein
• the flavonoid is apigenin;
• and
• the linker is a group having 3 or 4 ethylene glycol units.

A method of reducing resistance of a drug in a parasitic disease including the step of administering an effective amount of a compound of formula I:

• flavonoid-linker-flavonoid I
• wherein
• the flavonoid is apigenin;
• and
• the linker is a group having 3 or 4 ethylene glycol units.