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US 12,054,470 B2Granted
Photoswitchable dibenzothienylmethyl triphenylphosphonium derivatives and methods of treating cancer therewith
AssigneeSaint Louis University
InventorsRyan D. McCulla, Ankita Isor, Christopher Kent Arnatt
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Abstract
In one aspect, the present disclosure provides a compound of the formula: In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein.
Claims18
A compound of formula:
- wherein:
- R1 is —Y1-R2;
- wherein:
- Y1 is C1-C6 alkanediyl, substituted C1-C6 alkanediyl, or a linker of the formula:
- —Y2-A1-Y3
- wherein:
- Y2 and Y3 are each independently C1-C6 alkanediyl or substituted C1-C6 alkanediyl;
- A1 is —C(O)O— or —C(O)NH—;
- and
- R2 is P(R3)(R3′)(R3″)+X1−;
- wherein:
- R3, R3′, and R3″ are each independently C6-C12 aryl or substituted C6-C12 aryl;
- and
- X1″ is a monovalent anion;
- or a pharmaceutically acceptable salt thereof.
12 more elements
A method of making a compound of formula:
- wherein:
- R1 is —Y1—R2;
- wherein:
- C1-C6 alkanediyl, substituted C1-C6 alkanediyl, or a linker of the formula:
- —Y2-A1-Y3
- wherein:
- Y2 and Y3 are each independently C1-C6 alkanediyl or substituted C1-C6 alkanediyl;
- A1 is —C(O)O— or —C(O)NH—;
- and
- R2 is P(R3)(R3′)(R3″)+X1−;
- wherein:
- R3, R3′, and R3″ are each independently C6-C12 aryl or substituted C6-C12 aryl;
- and
- X1− is a monovalent anion;
- comprising:
- (A) reacting a compound of the formula:
- wherein:
- R1 is —Y1—R2′;
- wherein:
- Y1 is C1-C6 alkanediyl, substituted C1-C6 alkanediyl, or a linker of the formula:
- —Y2-A1-Y3
- wherein:
- Y2 and Y3 are each independently C1-C6 alkanediyl or substituted C1-C6 alkanediyl;
- A1 is —C(O)O— or —C(O)NH—;
- and
- R2′ is halo;
- in the presence of an oxidizing agent to form a compound of the formula:
- wherein:
- R1 is —Y1—R2′;
- wherein:
- Y1 is C1-C6 alkanediyl, substituted C1-C6 alkanediyl, or a linker of the formula:
- —Y2-A1-Y3
- wherein:
- Y2 and Y3 are each independently C1-C6 alkanediyl or substituted C1-C6 alkanediyl;
- A1 is —C(O)O— or —C(O)NH—;
- and
- R2′ is halo;
- and
- (B) reacting the compound prepared in step A with a compound of the formula:
- P(R3)(R3′)(R3″)
- wherein:
- R3, R3′, and R3″ are each independently C6-C12 aryl or substituted C6-C12 aryl.
39 more elements
A compound of formula:
- wherein:
- R4 is—Y4-R5;
- wherein:
- Y4 is a linker of the formula:
- —Y5-A2-Y6
- wherein:
- Y5 and Y6 are each independently C1-C6 alkanediyl or substituted C1-C6 alkanediyl;
- A2 is —C(O)O— or —C(O)NH—;
- and
- R5 is P(R6)(R6′)(R6″)+X2−;
- wherein:
- R6, R6′, and R6″ are each independently C6-C12 aryl or substituted C6-C12 aryl;
- and
- X2− is a monovalent anion;
- or a pharmaceutically acceptable salt thereof.
12 more elements
Dependencies are inferred from the claim text.