Thymoquinone/harmaline and related reaction products
New compositions of matter useful for the treatment of human diabetes and cancers comprise the reaction products of thymoquinone and harmaline or harmaline-like compounds, such as β-carboline compounds, and the derivatives, solvates, prodrugs, isomers, and tautomers of such compounds.
1. A composition containing one or more of the following compounds, and the derivatives, solvates, prodrugs, isomers, tautomers, esters, metal complexes, and salts thereof:
2. The composition of claim 1 , compounds having a molecular weight of about 540.
3. A composition of matter comprising a compound of the structure, and the derivatives, solvates, prodrugs, isomers, tautomers, esters, metal complexes, and salts thereof:
where the six-membered A ring is either phenyl or cyclohexadiene, R1 is a C1-C4 alkyl group, R2 is H or a C1-C4 alkyl group, R3 and R4 are independently either —OH or ═O, and the dotted bond line refers to the fact that the bond between the 1 position on the A ring and the intermediate CH2 or CH group of the linker between the A ring and the six-membered, N-containing pyridyl ring may be either a single bond or a double bond.
4. A composition of matter comprising a compound of the structure, and the derivatives, solvates, prodrugs, isomers, tautomers, esters, metal complexes, and salts thereof:
where each six-membered A ring is independently either phenyl or cyclohexadiene, each R1 is independently a C1-C4 alkyl group, each R2 is independently H or a C1-C4 alkyl group, each R3 and R4 are independently either —OH or ═O, and each dotted bond line refers to the fact that the bond between the 1 position on the A ring and the intermediate CH2 or CH group of the linker between the A ring and the six-membered, N-containing pyridyl ring may be either a single bond or a double bond, and wherein the A rings may be the same of different.
5. A method of preparing a composition comprising the steps of mixing together thymoquinone and a β-carboline compound in a non-interfering solvent, allowing the reaction to occur, and recovering the reaction product of the reaction.
6. The reaction product derived from the method of claim 5 .
7. A method of treating human diabetes by administering to a diabetic patient a composition in accordance with claim 6 .
8. A method of treating human cancer by administering to a diabetic patient a composition in accordance with claim 1 .
9. The composition of claim 1 , said composition comprising a compound of the below formula, and the isomers, tautomers, esters, metal complexes, and salts thereof.
10. The composition of claim 1 , including the isomers, tautomers, esters, metal complexes, and salts of the compounds of the formulas I-VIIIF, inclusive.
11. The composition of matter of claim 3 , and the isomers, tautomers, esters, metal complexes, and salts thereof.
12. The composition of matter of claim 4 , and the isomers, tautomers, esters, metal complexes, and salts thereof.