Inhibition by 3-deoxyflavonoids of T-lymphocyte activation and therapies related thereto

A compound of the formula:

• 3
• Wherein,
• X is selected from O and S;
• and
• i) when X is O,
• R1, R4, R5 and R8 are H or F;
• R6 and R7 combine to form a double bond;
• R2 and R3 are selected from H, OH, SH, Halogen, Alkyl, Amino, HNME, Cyano, Carboxyl, Carboxyalkyl, Carboxamide, alkoxycarbonyl, O-Hydroxyalkyl, CF3, O-Alkyl, O—SO3H, O—SO2H, O—PO3H, O-Glycoside, O-Glucoronide and O-Amino Acid, including O—CO—A—(CH2)n—NR′R″, where A is Phenyl, substituted phenyl or absent;
• n is 0 through 5;
• R′ and R″ are selected from H, lower alky hydroxyalkyl, mono and dialkylaminoalkyl, carboxyalkyl or R′ and R″ may combine to form a cyclic ring, optionally substituted with a O, S, NH or N-Alkyl and the methylene adjacent to the nitrogen may be optionally substituted with a amino alkyl, carboxy or carboxyalkyl group and O—CO—NH—(CH2)m—CH—(NH2)COOH, where m is 1 through 4;
• and when R2 and R3 are OH, SH or Amino, they may be optionally combined through a methylene or carbonyl group;
• R9 is selected from OH, Amino, NHMe, SH, or SMe;
• and
• R10 and R11 or R11 and R12 are methylenedioxy (O—CH2—O), or a cyclic carbonate (O—CO—O), or R12 is H and R10, R11, are selected from H, OH, Halogen such as F or Cl, Alkyl, Amino, Cyano, Carboxyl, Carboxyalkyl, Carboxamide, alkoxycarbonyl, O-Hydroxyalkyl, CF3, O-Alkyl, O—SO3H, O—SO2H, O—PO3H, O-Glycoside, O-Glucoronide and O-Amino Acid, including O—CO—A—(CH2)n—NR′R″, where A is Phenyl, substituted phenyl or absent;
• n is 0 through 5;
• R′ and R″ are selected from H, lower alkyl, hydroxyalkyl, aminoalkyl, mono and dialkylaminoalkyl, carboxyalkyl or R′ and R″ may combine to form a cyclic ring, optionally substituted with a O, S, NH or N-Alkyl and the methylene adjacent to the nitrogen may be optionally substituted with a amino alkyl, carboxy or carboxyalkyl group and O—CO—NH—(CH2)m—CH—(NH2)COOH, where m is 1 through 4;
• with the proviso that when R2 and/or R3 are H, OH, OMe, Cl, or Amino then R9, R10, and R11 are not the same.
• ii) when X is S,
• R1 through R5 and R9 through R12 are selected from H, OH, Halogen such as F or Cl, SH, SMe, Alkyl, Amino, NHMe, Cyano, Carboxyl, Carboxyalkyl, Carboxamide, alkoxycarbonyl, O-Hydroxyalkyl, CF3, O-Alkyl, O—SO3H, O—SO2H, O—PO3H, O-Glycoside, O-Glucoronide and O-Amino Acid, including O—CO—A—(CH2)n—NR′R″, wherein A is phenyl, substituted phenyl or absent;
• wherein n is 0 through 5, wherein R′ and R″ are selected from H, lower alkyl, hydroxyalkyl, aminoalkyl, mono and dialkylaminoalkyl, carboxyalkyl or wherein R′ and R″ combine to form a cyclic ring, said cyclic ring being optionally substituted with a O, S, NH or N-Alkyl and wherein the methylene adjacent to the nitrogen may be optionally substituted with a amino alkyl, carboxy or carboxyalkyl group and O—CO—NH—(CH2)m—CH—(NH2)COOH wherein m is 1 through 4;
• R6 and R7 combine to form a double bond;
• R8 is selected from H or F;
• and,
• when R1 through R5 and R9 through R12 are OH and/or amino, and are present on adjacent ring carbons then they may be combined through a methylene (—O—CH2—O—) or a carbonyl (—O—CO—O—, —O—CO—NH— or S—CO—NH—) group to form a cyclic ring.