SUBSTITUTED AURONE DERIVATIVES

A method for treating a microbial infection is disclosed. The method includes administering to a patient a pharmaceutical composition containing a compound of formula (IA) where each R is independently H, OH, Br, Cl, I, amino, thiol, nitro, C1-4 alkoxy, C1-4 alkenyloxy, C2-6 alkoxyalkyleneoxy, C1-4 alkylthio, C3-18 alkyl, or C3-18 alkenyl; or two adjacent R's, taken together, are a C2-18 bivalent moiety containing at least one oxygen atom, substituted or disubstituted with A or B or both, A being H, OH, Br, Cl, I, amino, or thiol, and B being H, C1-10 alkyl, C2-18 alkenyl, or C6-18 aryl; provided at least two Rs are not H; further provided that when each of two Rs is one of OH, C1-4 alkoxy, C1-4 alkenyloxy, or C2-6 alkoxyalkyleneoxy, and X is phenyl substituted with two substituents independently selected from OH, alkoxy, and alkenyloxy, the remaining R cannot be prenyl; further provided that when each of two Rs is one of OH, C1-4 alkoxy, C1-4 alkenyloxy, or C2-6 alkoxyalkyleneoxy, and X is phenyl substituted with three substituents independently selected from OH, alkoxy, and alkenyloxy, the remaining R cannot be prenyl; further provided that when each of two Rs is one of OH, C1-4 alkoxy, C1-4 alkenyloxy, or C2-6 alkoxyalkyleneoxy, and X is phenyl subsituted with a prenyl substituent and with two additional substituents independently selected from OH, alkoxy, and alkenyloxy, the remaining R cannot be H or OH; further provided that when each of two Rs is one of OH, C1-4 alkoxy, C1-4 alkenyloxy, or C2-6 alkoxyalkyleneoxy, and X is phenyl subsituted with a substituent containing three rings and with two additional substituents independently selected from OH, alkoxy, and alkenyloxy, the remaining R cannot be prenyl; X is C4-10 alkyl, C4-20 alkenyl, or a C4-20 single, C6-20 bridged, or C6-20 fused ring moiety containing cycloalkyl, cycloalkenyl, aryl, heterocycle, or heteroaryl, where X is substituted with H, OH, Cl, Br, I, amino, cyano, nitro, alkyl, alkoxy, alkenyl, or alkenyloxy; provided that if X is a heteroaryl or heterocyclic moiety where two Rs are each OH and meta to each other, then the remaining R is H and ortho to each of the two hydroxyls, and Y and Z are each O, and a ring atom of X is linked directly to the sp carbon atom adjacent to X, then substituted with H, OH, Cl, Br, I, amino, cyano, alkyl, alkoxy, alkenyl, or alkenyloxy; and each of Y and Z is independently selected from O, S, and NH; or a pharmaceutically acceptable salt or ester thereof.