Triterpenes having human antifungal and antiyeast activity

A therapeutic method of treating a mammal afflicted with a fungal infection comprising administering to the mammal an effective anti-fungal amount of a triterpene of formula (I):

• wherein
• R1 is hydrogen or hydroxy;
• R2 is a direct bond, carbonyl, oxy, thio, carbonyl oxy, oxy carbonyl, (C6-C10)aryl, or (C1-C6)alkyl;
• R3 is hydrogen, hydroxy, (C1-C6)alkyl, O═P(OH)2, O═P(OH)2OP(O)(OH)—, (C1-C5)alkanoyl, Si(R)3 wherein each R is H, phenyl or (C1-C6)alkyl, C(O)N(R)2, benzyl, benzoyl, tetrahydropyran-2-yl, 1-[(C1-C4)alkoxy](C1-C4)alkyl, or a glycoside;
• R4 is hydrogen, hydroxy, (C1-C6)alkyl, O═P(OH)2, O═P(OH)2OP(O)(OH)—, (C1-C5)alkanoyl, Si(R)3 wherein each R is H, phenyl or (C1-C6)alkyl, C(O)N(R)2, benzyl, benzoyl, tetrahydropyran-2-yl, 1-[(C1-C4)alkoxy](C1-C4)alkyl, or a glycoside;
• or R4 and R5 together are oxo;
• and
• R5 is direct bond, carbonyl, oxy, thio, carbonyl oxy, oxy carbonyl, (C6-C10)aryl, or (C1-C6)alkyl;
• or R4 and R5 together are oxo;
• wherein any alkyl can optionally be substituted with one or more halo, hydroxy, (C6-C10)aryl, nitro, cyano, (C1-C6)alkoxy, trifluoromethyl, polyethyleneimine, poly(ethylene glycol), oxo NR7R8, wherein R7 and R8 are each independently hydrogen, (C1-C6)alkyl or polyethyleneimine;
• or C(═O)OR9, wherein R9 is hydrogen, (C1-C6)alkyl, or polyethyleneimine;
• the bond between carbons 1 and 2 is a single bond or a double bond;
• wherein any alkyl is optionally interrupted on carbon with one or more oxy, thio, sulfinyl, sulfonyl, polyethyleneimine, or poly(ethylene glycol);
• wherein any alkyl is optionally partially unsaturated;
• wherein any aryl can optionally be substituted with one or more halo, hydroxy, nitro, cyano, (C1-C6)alkoxy, trifluoromethyl, polyethyleneimine, poly(ethylene glycol), oxo, NR7R8, wherein R7 and R8 are each independently hydrogen, (C1-C6)alkyl or polyethyleneimine;
• or C(═O)OR9, wherein R9 is hydrogen, (C1-C6)alkyl, or polyethyleneimine;
• or a pharmaceutically acceptable salt thereof, wherein the fungal infection is caused by a dermatophytic fungus, Candida albicans, or Candida guilliermondii.