Triterpenoids and compositions containing the same

A triterpenoid compound having the structure of Formula I, or a dimer thereof:

• wherein,
• at least one of X1 and X2 is ORa, NRaRb, or SRa, and the other of X1 and X2 is hydrogen, ORa, NRaRb, or SRa, wherein
• Ra is a hydrogen, cyano, —CF3, nitro, amino, or substituted or unsubstituted heteroaryl group;
• Rb is hydrogen, hydroxyl, alkyl, aryl, aralkyl, acyl, alkoxy, aryloxy, acyloxy, alkylamino, arylamino, amido, or a substituted version of any of these groups;
• or a substituent convertible in vivo to hydrogen;
• provided that Ra is absent when the atom to which it is bound is part of a double bond, further provided that when Ra is absent the atom to which it is bound is part of a double bond;
• Y is CH2 or CH2—CH2;
• Z is a covalent bond, —C(═O)—, alkanediyl, alkenediyl, alkynediyl, or a substituted version of any of these groups;
• the dashed bonds can be independently present or absent;
• R1, R2, R3 and R4 are each independently a hydrogen, hydroxyl, alkyl, substituted alkyl, alkoxy or substituted alkoxy group;
• at least one of R5, R6, R7, R8, R9 or R10 is independently —OMs, —CH2OMs, —C(═O)C≡CRa, —C≡CCO2Ra, —C≡CSO2Ra, —C≡CC(═O)Ra or —SO2Ra, or
• R5 and R6, or R7 and R8, or R9 and R10 are together ═CRdRd, wherein
• Rc is hydrogen or alkylthiyl, and
• Rd is hydrogen, halo, alkylthiyl, or substituted or unsubstituted alkylsulfonyl or alkylsulfonyl —O—;
• the remainder of R5, R6, R7, R8, R9 and R10 are independently hydrogen, hydroxyl, halo, cyano, ═O, —C≡CRa, CO2Ra, —CORa, alkyl, alkenyl, alkynyl, aryl, aralkyl, heteroaryl, heteroaralkyl, acyl, alkoxy, aryloxy, acyloxy, alkylamino, arylamino, nitro, amino, amido, —C(O)Re or a substituted version of any of these groups, wherein
• Re is hydrogen, hydroxy, halo, amino, hydroxyamino, azido or mercapto;
• or C1-C15-alkyl, C2-C15-alkenyl, C2-C15-alkynyl, C6-C15-aryl, C7-C15-aralkyl, C1-C15-heteroaryl, C2-C15-heteroaralkyl, C1-C15-acyl, C1-C15-alkoxy, C2-C15-alkenyloxy, C2-C15-alkynyloxy, C6-C15-aryloxy, C7-C15-aralkyloxy, C1-C15-heteroaryloxy, C2-C15-heteroaralkyloxy, C1-C15-acyloxy, C1-C15-alkylamino, C2-C15-dialkylamino, C1-C15-alkoxyamino, C2-C15-alkenylamino, C2-C15-alkynylamino, C6-C15-arylamino, C7-C15-aralkylamino, C1-C15-heteroarylamino, C2-C15-heteroaralkylamino, C1-C15-alkylsulfonylamino, C1-C15-amido, C1-C15-alkylsilyloxy, or substituted versions of any of these groups;
• R11 and R12 are each independently hydrogen, hydroxyl, halo, alkyl, alkenyl, alkynyl, aryl, aralkyl, heteroaryl, heteroaralkyl, acyl, alkoxy, aryloxy, aralkoxy, heteroaryloxy, hetero-aralkoxy, acyloxy, alkylamino, dialkylamino, arylamino, aralkylamino, heteroarylamino, heteroaralkylamino, amido, or a substituted version of any of these groups, or
• R11 and R12 are taken together and are alkanediyl, alkenediyl, arenediyl, alkoxydiyl, alkenyloxydiyl, alkylaminodiyl, alkenylaminodiyl, or alkenylaminooxydiyl;
• R13 is hydrogen, hydroxy or oxo;
• R14 is hydrogen or hydroxyl;
• and
• R15 is
• a hydrogen, hydroxyl, —NRfRg, cyano, halo, azido, phosphate, 1,3-dioxoisoindolin-2-yl, mercapto, silyl or —COOH group,
• substituted or unsubstituted versions of C1-C15-alkyl, C2-C15-alkenyl, C2-C15-alkynyl, C6-C15-aryl, C7-C15-aralkyl, C1-C15-heteroaryl, C2-C15-heteroaralkyl, C1-C15-acyl, C1-C15-alkoxy, C2-C15-alkenyloxy, C2-C15-alkynyloxy, C6-C15-aryloxy, C7-C15-aralkyloxy, C1-C15-heteroaryloxy, C2-C15-heteroaralkyloxy, C1-C15-acyloxy, C1-C15-alkylamino, C2-C15-alkenylamino, C2-C15-alkynylamino, C6-C15-arylamino, C7-C15-aralkylamino, C1-C15-heteroarylamino, C2-C15-heteroaralkylamino, C1-C15-amido, C1-C15-alkylthio, C2-C15-alkenylthio, C2-C15-alkynylthio, C6-C15-arylthio, C7-C15-aralkylthio, C1-C15-heteroarylthio, C2-C15-heteroaralkylthio, C1-C15-acylthio, C1-C12-thioacyl, C1-C12-alkylsulfonyl, C2-C12-alkenylsulfonyl, C2-C12-alkynylsulfonyl, C6-C12-arylsulfonyl, C7-C12-aralkylsulfonyl, C1-C12-heteroarylsulfonyl, C1-C12-heteroaralkylsulfonyl, C1-C12-alkylsulfinyl, C1-C12-alkenylsulfinyl, C2-C12-alkynylsulfinyl, C6-C12-aryl sulfinyl, C7-C12-aralkylsulfinyl, C1-C12-heteroarylsulfinyl, C1-C12-heteroaralkylsulfinyl, C1-C12-alkylphosphonyl, C1-C12-alkylphosphate, C2-C12-dialkylphosphate, C1-C12-alkylammonium, C1-C12-alkylsulfonium, C1-C15-alkylsilyl, or a substituted version of any of these groups,
• a —CO2Me, carbonyl imidazole, —CO-D-Glu(OAc)4, —CONH2, —CONHNH2, —CONHCH2CF3, or —C(═O)-heteroaryl group, or
• Z and R15 form a three to seven-membered ring, such that Z and R15 are further connected to one another through one or more of —O— and alkanediyl, further wherein Z is —CH— and R15 is —CH2— or Z, R15, and carbon numbers 13, 17 and 18 form a ring such that R15 is bound to carbon 13, wherein Y is methanediyl or substituted methanediyl and R15 is —O—, wherein
• Rf and Rg are independently hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, aryl, aralkyl, heteroaryl, heteroaralkyl, acyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy, aralkoxy, heteroaryloxy, heteroaralkoxy, thioacyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, arylsulfonyl, aralkylsulfonyl, heteroarylsulfonyl, or heteroaralkylsulfonyl, or a substituted version of any of these groups.