Analogs of terpene trilactones from ginkgo biloba for bioorganic and imaging studies

A compound having the structure:

• 34
• wherein R1 is H, or OH;
• wherein R2 is H, OH, F, Br, unsubstituted or substituted, straight or branched alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, or a alkynyl group having 1 to 5 carbon atoms;
• wherein R3 is H or OH;
• and
• wherein R4 is H, OH, -A-Ar, -A-Z-Ar, —SO2—Ar, or -A-NR5, or —R6,
• where A is an alkylene group having 1 to 8 carbon atoms, which is unsubstituted or substituted by a straight or branched alkyl chain group having 1 to 5 carbon atoms;
• Z is carbon, oxygen, sulfur or nitrogen;
• Ar is a phenyl group, a pyridyl group, a naphthyl group, a pyrimidyl group, or a quinolyl group, each of which may contain heteroatoms and may be unsubstituted or substituted by one to five substituents selected from the group consisting of hydrogen, halogen, a hydroxy group, a carboxylic acid group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 1 to 10 carbon atoms, an alkynyloxy group having 1 to 10 carbon atoms, a haloalkoxy group having 1 to 10 carbon atoms, a phenyl group, a phenoxy group, an aralkyl group, an aralkyloxy group, a substituted phenyl group, a substituted phenoxy group, a substituted aralkyl group, a substituted aralkyloxy group, —COR5, —COR6, —CONR5R6, —CO2R5, —NHCOR5, —NH(OH), —N(OH)COR5, —CHOR5, —OCH2CO2R5, —CH2SR5, —CH2NR5R6, —SR5, —OSR5, —O2NR5R6, —NR5R6, —NR5SO2R6,
• in which R5 and R6 are the same or different and each is hydrogen, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, —SCX3 in which X is a halogen, —CN, —NO2 or -Z-A-Z′- in which Z and A are as defined above and Z′ represents carbon, oxygen, sulfur, or nitrogen,
• or an optically pure enantiomer, or a salt of the compound.

A compound having the structure:

• 36
• wherein R4 is H, OH, -A-Ar, -A-Z-Ar, —SO2—Ar, or -A-NR5, or —R6,
• where A is an alkylene group having 1 to 8 carbon atoms, which is unsubstituted or substituted by a straight or branched alkyl chain group having 1 to 5 carbon atoms;
• Z is carbon, oxygen, sulfur or nitrogen;
• Ar is a phenyl group, a pyridyl group, a naphthyl group, a pyrimidyl group, or a quinolyl group, each of which may contain heteroatoms and may be unsubstituted or substituted by one to five substituents selected from the group consisting of hydrogen, halogen, a hydroxy group, a carboxylic acid group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 1 to 10 carbon atoms, an alkynyloxy group having 1 to 10 carbon atoms, a haloalkoxy group having 1 to 10 carbon atoms, a phenyl group, a phenoxy group, an aralkyl group, an aralkyloxy group, a substituted phenyl group, a substituted phenoxy group, a substituted aralkyl group, a substituted aralkyloxy group, —COR5, —COR6, —CONR5R6, —CO2R5, —NHCOR5, —NH(OH), —N(OH)COR5, —CHOR5, —OCH2CO2R5, —CH2SR5, —CH2NR5R6, —SR5, —OSR5, —O2NR5R6, —NR5R6, —NR5SO2R6,
• in which R5 and R6 are the same or different and each is hydrogen, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, —SCX3 in which X is a halogen, —CN, —NO2 or -Z-A-Z′- in which Z and A are as defined above and Z′ represents carbon, oxygen, sulfur, or nitrogen,
• or an optically pure enantiomer, or a salt of the compound.