One-step synthesis of phosphate-based inhibitors and applications thereof
AssigneesUniversity of South Carolina, North Carolina State University
InventorsEdward D'Antonio, Joshua Pierce
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Abstract
One-step methods for forming phosphate-based enzyme inhibitors are disclosed. Methods include reacting o-phosphorylethanolamine with an acyl chloride at acidic conditions. Acyl chlorides can be derivatized. The phosphate-based enzyme inhibitors can inhibit enzymes of the pentose phosphate pathway including D-ribose-5-phosphate aldose-ketose isomerase enzymes such as T. cruzi ribose 5-phosphate isomerase type B and D-ribulose-5-phosphate 3-epimerase enzymes. Methods can be used in forming pharmaceutical compositions for use in treatment of disease caused by kinetoplastid parasites including T. cruzi, T. brucei, and Leishmania spp.
Claims12
A method for forming a phosphate-based enzyme inhibitor, the method comprising:
- combining o-phosphorylethanolamine with phenylacetyl chloride having the following structure:
- to form a reaction mixture;
- and
- maintaining the reaction mixture at a pH of from about 4 to about 6, wherein the phosphate-based enzyme inhibitor is a D-ribose-5-phosphate aldose-ketose isomerase inhibitor and/or a D-ribulose-5-phosphate 3-epimerase inhibitor.
A pharmaceutical composition comprising:
- a phosphate-based enzyme inhibitor having the following structure:
- in which R2 is hydrogen, halogen, C1-C4 alkyl halogen, C1-C4 alkyl, or C1-C4 alkoxy;
- and
- a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.