Antifungal enediynes
AssigneePhytera, Inc.
InventorsBaoliang Cui, James Bruce McAlpine, Maureen Kelly Talbot, Shu-Wei Yang, Catherine Heintz, Angela Stafford
Life of this patent
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Abstract
The invention features enediynes and methods for their production and use. The enediynes of the invention have the formula: wherein R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction; each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive; R3 is a pyrrole, furan, or thiophene ring; and X is an integer between 4 and 10, inclusive.
Claims30
A substantially pure compound having the formula:
- wherein —C2H2—C4—R3 is —CH═CH—C≡C—C≡C—R3;
- R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction;
- each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive;
- R3 is a pyrrole, furan, or thiophene ring;
- and X is an integer between 4 and 10, inclusive.
A pharmaceutical composition comprising a compound having the formula:
- and a pharmaceutically acceptable carrier, wherein —C2H2—C4—R3 is —CH═CH—C≡C—C≡C—R3;
- R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction;
- each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive;
- R3 is a pyrrole, furan, or thiophene ring;
- and X is an integer between 4 and 10, inclusive.
A substantially pure compound having the formula:
- wherein —(C2H2)—C4—R3 is —(CH═CH)—C≡C—C≡C—R3;
- R1 is OH, NH2, OCH3, or OC2H5, R3 is a pyrrole, furan, or thiophene ring, and X is an integer between 5 and 7, inclusive.
A method of inhibiting the growth of a fungal cell, said method comprising the step of contacting the cell with a cell-killing amount of a compound having the formula:
- wherein —C2H2—C4—R3 is —CH═CH—C≡C—C≡C—R3;
- R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction;
- each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive;
- R3 is a pyrrole, furan, or thiophene ring;
- and X is an integer between 4 and 10, inclusive.
A method of inhibiting the development of a fungal infection in an organism, said method comprising the step of contacting the organism with a compound having the formula:
- wherein —C2H2—C4—R3 is —CH═CH—C≡C—C≡C—R3;
- R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction;
- each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive;
- R3is a pyrrole, furan, or thiophene ring;
- and X is an integer between 4 and 10, inclusive.
A compound for treating a fungal infection, the compound having the formula:
- wherein —C2H2—C4—R3 is —CH═CH—C≡C—C≡C—R3;
- R1 is a hydroxyl group or a moiety that can be replaced by a hydroxyl group in a hydrolysis reaction;
- each R2 is, independently, H or a monovalent hydrocarbon moiety containing between 1 and 4 carbon atoms, inclusive;
- R3 is a pyrrole, furan, or thiophene ring;
- and X is an integer between 4 and 10, inclusive.
Dependencies are inferred from the claim text.