Carbon monoxide releasing molecules and associated methods
The present disclosure relates to carbon monoxide releasing molecules (“CORMs”), and methods of synthesizing and applying the molecules. More specifically, this disclosure relates to structurally tunable CORMS, compounds containing CORMS (and salts thereof). An exemplary compound includes:
1. A compound, or salt thereof, comprising the formula:
wherein:
Y is a member selected from the group consisting of O or S;
X is a member selected from the group consisting of O or S;
R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 are each a member selected from the group consisting of —H, —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′) 2 , —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, —OSO 2 R′, —C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 alkyl-C 5-15 aryl, C 2-12 alkenyl-C 5-15 aryl, an amino acid, an aminoglycoside, a carbohydrate, and a heterocycle containing O, N, or S;
wherein the —C 5-15 aryl is optionally substituted with —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′), —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, or —OSO 2 R′;
wherein the —C 1-12 alkyl, the —C 2-12 alkenyl, the C 2-12 alkynyl, the C 1-12 alkyl-C 5-15 aryl, the C 2-12 alkenyl-C 5-15 aryl, or the heterocycle is optionally substituted with —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′) 2 , —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, —OSO 2 R′, —P(aryl) 3 , P(alkyl) 3 , or PO 3 2 , or HPO 3 ;
wherein R′ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, and —C 2-12 alkenyl; and
R 3 is a member selected from the group consisting of —H, —COOH, —CSOH, —COOR″, —CONH 2 , —CONHR″, CON(R″) 2 , —COR″, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR″, —SH, —SR″, —O—CO—R″, —NH 2 , —NHR″, —NR 2 ″, —NH(R″) 2 , —NH—CO—R″, —NR″—CO—R″, —SO 3 R″, —OSO 2 R″, —P(aryl) 3 , P(alkyl) 3 , PO 3 2 , HPO 3 , C 5-15 aryl, C 1-12 alkyl, —C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 alkyl-C 5-15 aryl, C 2-12 alkenyl-C 5-15 aryl, amino acids, aminoglycosides, carbohydrates, or heterocycles containing O, N, or S;
wherein the C 5-15 aryl, the C 1-12 alkyl, the —C 2-12 alkenyl, the C 2-12 alkynyl, the C 1-12 alkyl-C 5-15 aryl, the C 2-12 alkenyl-C 5-15 aryl, or the heterocycle is optionally substituted with —COOH, —CSOH, —COOR″, —CONH 2 , —CONHR″, CON(R″) 2 , —COR″, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR″, —SH, —SR″, —O—CO—R″, —NH 2 , —NHR″, —NR 2 ′, —NH(R″) 2 , —NH—CO—R″, —NR″—CO—R″, —SO 3 R″, —OSO 2 R″, —P(aryl) 3 , P(alkyl) 3 , PO 3 2 , or HPO 3 ;
wherein R″ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, and C 2-12 alkynyl, each of which is optionally unsubstituted or substituted with phosphonium; and
R 9 is —H or —COR″″,
wherein R″″ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, and C 2-12 alkynyl.
2. The compound of claim 1 , wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are the same.
3. The compound of claim 1 , wherein the compound is:
4. The compound of claim 1 , wherein the compound is:
5. The compound of claim 1 , wherein the compound is:
6. The compound of claim 1 , wherein the compound is:
7. The compound of claim 1 , wherein the compound is:
8. The compound of claim 1 , wherein the compound is:
9. The compound of claim 1 , wherein the compound is:
10. The compound of claim 1 , wherein the compound is:
11. The compound of claim 1 , wherein the compound is:
12. The compound of claim 1 , wherein the compound is:
13. A composition, comprising the compound of claim 1 .
14. The composition of claim 13 , further comprising a pharmaceutically acceptable carrier.