Compounds for use in synthesis of peptidomimetics
View Patent ↗Synthesis of O-benzotriazole and O-imidazole synthons are described. Uses of synthons in synthesis of azapeptides and other peptidomimetics, azapeptides and other peptidomimetics synthesized from the synthons and uses of azapeptides and other peptidomimetics are also described.
1. A compound of Formula (IV):
wherein R is selected from the group consisting of side chain radicals of aspartic acid, phenylalanine, alanine, histidine, glutamic acid, tryptophan, valine, leucine, lysine, methionine, tyrosine, threonine, isoleucine, arginine, glycine, asparagine, serine, and glutamine; and
M is a substituent selected from the group consisting of a halogen, a C 1 -C 6 alkyl, hydroxyl, —COOH, —COH, methoxyl, ethoxyl, propoxyl, a C 1 -C 6 haloalkyl, —NH 2 , and —NH 3 .
2. The compound of claim 1 , wherein M is a halogen selected from the group consisting of Cl, F, and Br.
3. The compound of claim 1 , wherein M is a C 1 -C 6 haloalkyl selected from the group consisting of —CF 3 , —CHF 2 , —CH 2 F, —CBr 3 , —CHBr 2 , —CH 2 Br, —CCl 3 , —CHCl 2 , and —CH 2 Cl.
4. The compound of claim 3 , wherein the haloalkyl is —CF 3 .
5. The compound of claim 1 , wherein the side chain radical is substituted.
6. The compound of claim 5 , wherein the side chain radical is substituted with one or more substituents selected from the group consisting of a halogen, a C 1 -C 6 alkyl, hydroxyl, —COOH, —COH, methoxyl, ethoxyl, propoxyl, a C 1 -C 6 haloalkyl and a protecting group.
7. The compound of claim 6 , wherein the side chain radical is substituted with the C 1 -C 6 alkyl.
8. The compound of claim 6 , wherein the side chain radical is substituted with the C 1 -C 6 haloalkyl.
9. The compound of claim 6 , wherein the protecting group is selected from the group consisting of Phth, Boc, Fmoc, and Ddz.
10. The compound of claim 1 , wherein R is selected from the group consisting of side chain radicals of aspartic acid, histidine, glutamic acid, tryptophan, lysine, methionine, tyrosine, isoleucine, arginine, asparagine, and glutamine.
11. A compound of Formula (II):
wherein R is selected from the group consisting of substituted side chain radicals of aspartic acid, phenylalanine, alanine, histidine, glutamic acid, tryptophan, valine, leucine, lysine, methionine, tyrosine, threonine, isoleucine, arginine, glycine, asparagine, serine, and glutamine; and
M is a substituent selected from the group consisting of a halogen, a C 1 -C 6 alkyl, hydroxyl, —COOH, —COH, methoxyl, ethoxyl, propoxyl, a C 1 -C 6 haloalkyl, —NH 2 , and —NH 3 .
12. The compound of claim 11 , wherein M is a halogen selected from the group consisting of Cl, F, and Br.
13. The compound of claim 11 , wherein M is a C 1 -C 6 haloalkyl selected from the group consisting of —CF 3 , —CHF 2 , —CH 2 F, —CBr 3 , —CHBr 2 , —CH 2 Br, —CCl 3 , —CHCl 2 , and —CH 2 Cl.
14. The compound of claim 13 , wherein the haloalkyl is —CF 3 .
15. The compound of claim 11 , wherein M is a C 1 -C 6 alkyl.
16. The compound of claim 11 , wherein the side chain radical is substituted with one or more substituents selected from the group consisting of a halogen, a C 1 -C 6 alkyl, hydroxyl, —COOH, —COH, methoxyl, ethoxyl, propoxyl, a C 1 -C 6 haloalkyl and a protecting group.
17. The compound of claim 16 , wherein the side chain radical is substituted with the C 1 -C 6 alkyl.
18. The compound of claim 16 , wherein the side chain radical is substituted with the C 1 -C 6 haloalkyl.
19. The compound of claim 16 , wherein the protecting group is selected from the group consisting of Phth, Boc, Fmoc, and Ddz.
20. The compound of claim 11 , wherein R is selected from the group consisting of side chain radicals of aspartic acid, histidine, glutamic acid, tryptophan, lysine, methionine, tyrosine, isoleucine, arginine, asparagine, and glutamine.