Flavan-3-ol analogs and anti-inflammatory activity

A compound of Formula 1:

• or a pharmaceutically acceptable salt thereof, wherein
• m is a whole number selected from 1-3;
• n is a whole number selected from 1-3;
• p is a whole number selected from 1-2;
• q is a whole number selected from 2-6;
• R1 is
• R2 is —OR, —O(C═O)R7, —O(C═O)OR7, —O(C═O)N(R7)2, or —O(P═O)(OH)2;
• each of R3 and R4 is hydrogen;
• R5 for each instance is independently selected from the group consisting of halide, methyl, chloride, fluoride, and —OCH2OMe;
• R6 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, —OR, —SR, —NR2, —(C═O)R, —C(C═O)OR, —(C═O)NR2, —N(R)(C═O)R, —O(C═O)R, —N(R)(C═O)OR, —O(C═O)NR2, —SO2R, —SO2NR2, haloalkyl, perhaloalkyl, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, —OCH2OMe, and —(CR2)qR8;
• R7 for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, and —(CR2)qR8;
• or two instances of R7 taken together form a 5-6 membered cycloalkyl, heterocycloalkyl, or heteroaryl;
• R8 for each instance is independently selected from the group consisting of —OR, —SR, —NR2, —(C═O)R, —(C═O)OR, —(C═O)NR2, —N(R)(C═O)R, —O(C═O)R, —N(R)(C═O)OR, —O(C═O)NR2, —SO2R, and —SO2NR2;
• and
• R for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, and heteroaryl;
• or two instances of R taken together form a 5-6 membered heterocycloalkyl or heteroaryl;
• or
• a compound of Formula 2:
• or a pharmaceutically acceptable salt thereof, wherein
• m is a whole number selected from 1-2;
• q is a whole number selected from 2-6;
• R1 is
• or propyl;
• R2 is —OR, —O(C═O)R7, —O(C═O)OR7, —O(C═O)N(R7)2, or —O(P═O)(OH)2;
• R5 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, —OR, —NR2, haloalkyl, perhaloalkyl, alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, —OCH2OMe, and —(CR2)qR8;
• R6 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, —OR, —NR2, haloalkyl, perhaloalkyl, alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, —OCH2OMe, and —(CR2)qR8;
• R7 for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, and —(CR2)qR8;
• or two instances of R7 taken together form a 5-6 membered cycloalkyl, heterocycloalkyl, or heteroaryl;
• R8 for each instance is independently selected from the group consisting of —OR, —SR, —NR2, —(C═O)R, —(C═O)OR, —(C═O)NR2, —N(R)(C═O)R, —O(C═O)R, —N(R)(C═O)OR, —O(C═O)NR2, —SO2R, and —SO2NR2;
• and
• R for each instance is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, and heteroaryl;
• or two instances of R taken together form a 5-6 membered heterocyloalkyl or heteroaryl.