Curcuminoids, analogs thereof, and methods of making the same

Patent metadata

Field	Value
Publication number	US-12595222-B2
Application number	US-202217865037-A
Country	US
Kind code	B2
Filing date	Jul 14, 2022
Priority date	Jul 14, 2021
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

The present invention provides compounds including curcuminoids and analogs thereof, as well as methods of making the same. In various aspects, the method of making the compounds is free of added solvents.

First claim

What is claimed is:

1 . A compound having the structure:

wherein
X and Y are independently chosen from
substituted or unsubstituted aryl, and
substituted or unsubstituted heteroaryl; and

wherein
X and Y have different structures, or
X and Y are independently chosen from 2- nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-cholorophenyl, 3-cholorophenyl, 4-cholorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3,5-dimethoxyphenyl, 4-(trifluoromethyl)phenyl, 2-naphthyl, 6-methoxy-2-naphthyl, 3-methoxy-4hydroxyphenyl, 2-hydroxy-3-methoxyphenyl, 4- cyanophenyl,

the compound has the structure:

2 . The compound of claim 1 , wherein the compound is an analog of a curcuminoid.

3 . The compound of claim 1 , wherein X and Y have the same structure.

4 . The compound of claim 1 , wherein X and Y have different structures.

5 . The compound of claim 1 , wherein X and Y are independently chosen from 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3,5-dimethoxyphenyl, 4-(trifluoromethyl) phenyl, 2-naphthyl, 6-methoxy-2-naphthyl, 3-methoxy-4-hydroxyphenyl, 2-hydroxy-3-methoxyphenyl, 4-cyanophenyl,

6 . The compound of claim 1 , wherein X and Y independently have the structure:

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are independently chosen from —H, —OCH 3 , —Cl, —Br, —F, —I, —CN, —NO 2 , —CF 3 , and —N(CH 3 ) 2 .

7 . The compound of claim 1 , wherein the compound has the structure:

8 . The compound of claim 1 , wherein the compound has the structure:

9 . A method of making the compound of claim 1 , the method comprising:
combining
2-acetylcylohexanone, 2-acetylcyclopentanone, or 2-acetylcyclohexane-1,3-dione,
an aldehyde having the structure X—C(O)H and/or Y—C(O)H,
B 2 O 3 ,
R B —NH 2 , and
(R B O) 3 B,
to form the compound of claim 1 ; wherein R B is independently (C 1 -C 10 )alkyl.

10 . The method of claim 9 , wherein R B is n-butyl or isopropyl.

11 . The method of claim 9 , wherein the combining is performed in the absence of any added solvent.

12 . The method of claim 9 , wherein the combining is performed with heating to 40-100° C.

13 . The method of claim 9 , wherein the combining is performed with heating provided by microwave energy.

14 . A method of treating a disease, comprising:
administering the compound of claim 1 to a subject that has the disease.

15 . A method of making a compound, the method comprising:
combining
acetylacetone, 2-acetylcylohexanone, 2-acetylcyclopentanone, or 2-acetylcyclohexane-1,3-dione,
an aldehyde having the structure X—C(O)H and/or Y—C(O)H,
B 2 O 3 ,
R B —NH 2 , and
(R B O) 3 B, wherein R B is independently (C 1 -C 10 ) alkyl, to form the compound, wherein the compound has the structure:

wherein
A is —C—,
X and Y are independently chosen from
substituted or unsubstituted aryl, and
substituted or unsubstituted heteroaryl; and

wherein
X and Y have different structures, or
X and Y are independently chosen from 2- nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-cholorophenyl, 3-cholorophenyl, 4-cholorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3,5-dimethoxyphenyl, 4-(trifluoromethyl)phenyl, 2-naphthyl, 6-methoxy-2-naphthyl, 3-methoxy-4hydroxyphenyl, 2-hydroxy-3-methoxyphenyl, 4- cyanophenyl,

the compound has the structure:

16 . The method of claim 15 , wherein X and Y are independently chosen from 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3,5-dimethoxyphenyl, 4-(trifluoromethyl) phenyl, 2-naphthyl, 6-methoxy-2-naphthyl, 3-methoxy-4-hydroxyphenyl, 2-hydroxy-3-methoxyphenyl, 4-cyanophenyl,

17 . A compound having the structure:

wherein
A is —C—,
X and Y are independently chosen from
substituted or unsubstituted aryl, and
substituted or unsubstituted heteroaryl,

wherein X and Y have different structures, and
L is a substituted or unsubstituted linker group chosen form —(CH 2 ) 3 , —(CH 2 ) 2 —, and —CH 2 —CH 2 —C(O)—.

18 . A method of killing a microbe or decreasing the rate of proliferation of a microbe, the method comprising:
contacting the microbe and a compound having the structure:

wherein
A is —C—,
X and Y are independently chosen from
substituted or unsubstituted aryl, and
substituted or unsubstituted heteroaryl, and

L is a substituted or unsubstituted linker group chosen from —(CH 2 ) 3 —, —(CH 2 ) 2 —, and —CH 2 —CH 2 —C(O)—.

Assignees

• Wisys Tech Foundation Inc

Inventors

• Stepanova Valeria A

Classifications

• C07C45/72

  by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups · CPC title

• A01N35/02

  containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals · CPC title

• A01P1/00

  Disinfectants; Antimicrobial compounds or mixtures thereof · CPC title

• C07C49/255 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C49/683 Primary

  having unsaturation outside the aromatic rings · CPC title