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US 2019/0161461 A1Published application
Ribonucleotide reductase inhibitors and methods of use
AssigneeCity of Hope
InventorsDavid Horne, Christopher Lincoln
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Abstract
Provided herein are novel compounds that inhibit ribonucleotide reductase (RR) by binding to RRM2 and interfering with the activity of the RRM1/RRM2 holoenzyme, as well as methods of synthesizing these novel compounds. The compounds may be used to inhibit RR activity and to treat various conditions associated with RRM2 expression, such as for example certain cancer types, mitochondrial diseases, or degenerative diseases.
Claims15
A method of synthesizing a compound having the structure:
- comprising the steps:
- (a) converting veratrole to 1-(3,4-dimethoxyphenyl)-2-phenylethanone;
- (b) converting 1-(3,4-dimethoxyphenyl)-2-phenylethanone to 4-(3,4-dimethoxyphenyl)-5-phenylthiazol-2-amine;
- (c) converting 4-(3,4-dimethoxyphenyl)-5-phenylthiazol-2-amine to N-(4-(3,4-dimethoxyphenyl)-5-phenylthiazol-2-yl)-3,4-dimethoxybenzamide;
- and
- (d) converting N-(4-(3,4-dimethoxyphenyl)-5-phenylthiazol-2-yl)-3,4-dimethoxybenzamide to
3 more elements
A compound having the formula:
- wherein,
- R is substituted or unsubstituted aryl,
- R1, R2, R3, R4, R5, R6, and R7 are independently hydrogen, substituted or unsubstituted aryl, or a substituted or unsubstituted alkyl;
- and
- R8, R9, R10 and R11 are independently a hydroxyl protecting group, wherein R8 and R9 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl and R10 and R11 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl.
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A method of synthesizing a compound having the structure:
- said method comprising contacting a hydroxyl deprotecting agent with a compound having the formula:
- wherein,
- R is substituted or unsubstituted aryl,
- R1, R2, R3, R4, R5, R6, and R7 are independently hydrogen, substituted or unsubstituted aryl, or a substituted or unsubstituted alkyl;
- and
- R8, R9, R10 and R11 are independently hydroxyl protecting groups wherein R8 and R9 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl and R10 and R11 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl.
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Dependencies are inferred from the claim text.