IP Library Granted Patent US 11,932,607
Granted Patent B1
US 11,932,607 · App. 18/384,685 · Granted Mar 19, 2024

4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid as an antimicrobial compound

Inventors: Hany Mohamed Abd El-Lateef Ahmed (Al-Ahsa, SA); Mai Mostafa Khalaf Ali (Al-Ahsa, SA); Antar Ahmed Abdelhamid Ahmed (Sohag, EG); Amer A. Amer (Sohag, EG)
Assignee: KING FAISAL UNIVERSITY
C07D233/64A61P31/04A61P31/10
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Quick Facts
Patent No.
US 11,932,607
App. No.
18/384,685
Granted
Mar 19, 2024
Kind
B1
Abstract

An 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound, its synthesis, and its use as an antimicrobial agent.

Claims (17)

1. An 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound having the formula I:

2. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 1 and a pharmaceutically acceptable carrier.

3. A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 1 .

4. The method of treating the microbial infection of claim 3 , wherein the microbial infection is caused by one or more bacteria or fungi.

5. The method of treating the microbial infection of claim 4 , wherein the microbial infection is caused by one or more gram positive bacteria, one or more gram negative bacteria, one or more fungi, or a combination thereof.

6. The method of treating the microbial infection of claim 5 , wherein the one or more gram positive bacteria are Bacillus cereus, Staphylococcus aureus , or a combination thereof.

7. The method of treating the microbial infection of claim 5 , wherein the one or more gram negative bacteria are Pseudomonas aeruginosa, Escherichia coli , or a combination thereof.

8. The method of treating the microbial infection of claim 5 , wherein the one or more fungi are Aspergillus flavus, Chrysosporium keratinophilum , or a combination thereof.

9. A method of making the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 1 , the method comprising:

mixing 1,2-bis(4-chlorophenyl)ethane-1,2-dione, 4-chlorobenzaldehyde, 4-aminobenzoic acid, and ammonium acetate in pyridinium ionic liquid to obtain a solution;

irradiating the solution followed by cooling to room temperature to obtain a formed precipitate;

purifying the formed precipitate by filtering and recrystallization using ethanol; and

obtaining the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound.

10. The method of making the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 9 , wherein the irradiating step takes place in a sonicator for about 21 minutes.

11. The method of making the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 9 , wherein the irradiating step is conducted at about 50° C.

12. The method of making 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 9 , wherein the purifying step comprises collecting the formed precipitate by filtration and washing the formed precipitate with distilled water.

13. The method of making the 4-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)benzoic acid compound of claim 9 , wherein the 1,2-bis(4-chlorophenyl)ethane-1,2-dione, the 4-chlorobenzaldehyde, the 4-aminobenzoic acid, and the ammonium acetate are added in about a 1:1:1:1 molar ratio.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2023
From: AHMED, HANY MOHAMED ABD EL-LATEEF; ALI, MAI MOSTAFA KHALAF; AHMED, ANTAR AHMED ABDELHAMID; AMER, AMER A.
To: KING FAISAL UNIVERSITY
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