Substituted Hydroxystilbene Compounds and Derivatives, Synthesis and Uses Thereof

A process of synthesising a compound of formula (I):

• wherein:
• R1a is independently allyl, crotyl, prenyl, geranyl, farnesyl, benzyl, 2-alkenyl or 2-alkynyl;
• R1b is independently CF3, OH, OR2, NO2, NMe2, NMeEt, NHR3, NMeR3, NHC═NH(NH2) or COOR2;
• R1c is independently H, alkyl, alkenyl, alkynyl, alkanedienyl, prenyl, geranyl, farnesyl, or benzyl;
• R1d is independently CF3, OH, OR2, NHR3, NO2, NMeR3, NHC═NH(NH2) or COOR2;
• R1b and R1d are not the same;
• R1e is independently H, C1-C6 alkyl, OH, OR2, NO2, NMe2, NHR3, NMeR3, or SR2;
• R1f is independently H, OH, OR2, NO2, NHR3, N(OH)(CO)CH3, NHC═NH(NH2), COOR2, COOH;
• R1g is independently H, alkyl, CF3, OH or OR2;
• no more than one of R1e, R1f or R1g can be H;
• or R1e and R1f form a five or six-membered heterocyclic ring containing a carbonyl group or (CO)CH2 group when R1c is independently OH, NH2 or NHMe and R1f is NH2, such that the nitrogen of R1f is bridged with the carbonyl group or (CO)CH2 group to the oxygen or nitrogen of R1e;
• R2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, trifluoromethyl, COCOOR4 or an O-protecting group when R2 is attached to an O;
• R3 is independently H, CH3, OH, (CO)H, (CO)Me, SO2Me, CH2COOH, CH2COOR2, CO(CH2)nNH2, CONH2, CO(CH2)nCOOH or COCOOR4, where n is 0, 1 or 2;
• and
• R4 is C1-C6 alkyl;
• and
• the process comprising:
• i) a step of coupling a compound of formula (II) (Module A) with a compound of formula (III) (Module B) to afford a compound of formula (IV) (Module C):
• wherein,
• in Formula II (Module A):
• R2b is independently CF3, OH, OR2, NO2, NMe2, NMeEt, NHR3 or NMeR3;
• R2c is independently H, alkyl, alkenyl, alkynyl, alkanedienyl, prenyl, geranyl, farnesyl, or benzyl;
• R2d is independently CF3, OH, OR2, NO2, NHR3, NMeR3, NHC═NH(NH2) or COOR2;
• X is a halide or a hydroxyl group, wherein the halide is selected from the group consisting of F, Cl, Br, I, and At;
• R2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, trifluoromethyl, or O-protecting group when R2 is attached to an O;
• and
• R3 is independently H, OH, CH3, (CO)H, COMe, SO2Me, COCH2NH2, or CH2COOR2;
• in Formula III (Module B):
• R3e is independently H, C1-C6 alkyl, OH, OR2, NO2, NHMe, NMe2, NHR3, NMeR3 or SR2;
• R3f is independently H, OH, OR2, NO2, NHR3, NHC═NH(NH2), COOH or COOR2;
• R3g is independently H, alkyl, CF3, OH or OR2;
• and no more than one of R3e, R3f or R3g can be H;
• or R3e and R3f form a five or six-membered heterocyclic ring containing a carbonyl group or (CO)CH2 group when R3e is OH, NH2 or NHMe and R3f is NH2, such that the nitrogen of R3f is bridged with the carbonyl group or (CO)CH2 group to the oxygen or nitrogen of R3e;
• R2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, trifluoromethyl or O-protecting group when R2 is attached to an O,
• R3 is independently H, CH3, OH, (CO)H, COMe, SO2Me, COCH2NH2, CH2COOH or CH2COOR2;
• and
• R4 is C1-C6 alkyl;
• in Formula IV (Module C):
• R4b is independently CF3, OH, OR2, NO2, NMe2, NMeEt, NHR3 or NMeR3;
• R4e is independently H, alkyl, alkenyl, alkynyl, alkanedienyl, prenyl, geranyl, farnesyl, or benzyl;
• R4d is independently CF3, OH, OR2, OR3, NO2, NHR3, NMeR3, NHC═NH(NH2) or COOR2;
• R4e is independently H, C1-C6 alkyl, OH, OR2, NO2, NMe2, NHR3, NMeR3 NHC(O)H or SR2;
• R4f is independently H, OH, OR2, NO2, NHR3, NHC═NH(NH2), COOH or COOR2;
• R4g is independently H, alkyl, CF3, OH or OR2;
• and no more than one of R4e, R4f or R4g can be H;
• or R4e and R4f form a five or six-membered heterocyclic ring containing a carbonyl group or (CO)CH2 group when R4e is OH, NH2 or NHMe and R4f is NH2, such that the nitrogen of R4f is bridged with the carbonyl group or (CO)CH2 group to the oxygen or nitrogen of R4e;
• R2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, trifluoromethyl or O-protecting group when R2 is attached to an O;
• R3 is independently H, CH3, OH, (CO)H, COMe, SO2Me, COCH2NH2, CH2COOH or CH2COOR2;
• and
• X is a halide or a hydroxyl group, wherein the halide is selected from the group consisting of F, Cl, Br, I, and At.