# US 11,999,701 B1 · 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazol-1-yl as an antimicrobial compound

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- Number: US 11,999,701 B1
- Document ID: US11999701B1
- Status: Granted
- Kind: B1
- Application number: 18/382,972
- Filed: 2023-10-23
- Granted: 2024-06-04
- Earliest claimed: 2023-10-23
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Lateef Ahmed; Mai Mostafa Khalaf Ali; Amer A. Amer; Antar Ahmed Abdelhamid Ahmed
- Web page: https://patentgrep.com/patent/US11999701B1

## CPC

- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A61K 31/4164: 1,3-Diazoles
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound, its synthesis, and its use as an anticancer, anti-inflammatory, and/or antimicrobial agent.

## Claims

### Claim 1

A pharmaceutically acceptable composition comprising a therapeutically effective amount of a 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound and a pharmaceutically acceptable carrier, the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound having the formula I:

### Claim 2

A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount of a 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound having the formula I:

### Claim 3 (depends on 2)

The method of treating the microbial infection of claim 2, wherein the microbial infection is caused by one or more bacteria or fungi.

### Claim 4 (depends on 3)

The method of treating the microbial infection of claim 3, 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.

### Claim 5 (depends on 4)

The method of treating the microbial infection of claim 4, wherein the one or more gram positive bacteria are Bacillus cereus, Staphylococcus aureus, or a combination thereof.

### Claim 6 (depends on 4)

The method of treating the microbial infection of claim 4, wherein the one or more gram negative bacteria are Pseudomonas aeruginosa, Escherichia coli, or a combination thereof.

### Claim 7 (depends on 4)

The method of treating the microbial infection of claim 4, wherein the one or more fungi are Aspergillus flavus, Chrysosporium keratinophilum, or a combination thereof.

### Claim 8

A method of making a 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound, the method comprising:
adding 1,2-bis(4-chlorophenyl)ethane-1,2-dione, benzaldehyde, and ammonium acetate to acetic acid to obtain a reaction mixture;
exposing the reaction mixture to ultrasonic irradiation until reaction completion to obtain a formed precipitate;
purifying the formed precipitate by recrystallization using ethanol; and
obtaining the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound.

### Claim 9 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the exposure to ultrasonic irradiation can be in a sonicator.

### Claim 10 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the exposure to ultrasonic irradiation is at a temperature of about 45° C. to about 55° C.

### Claim 11 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the exposure to ultrasonic irradiation is for at least about 3 hours.

### Claim 12 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein after reaction completion the reaction mixture is washed with water.

### Claim 13 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the 1,2-bis(4-chlorophenyl)ethane-1,2-dione and benzaldehyde, are added in an about 1:1 molar ratio.

### Claim 14 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol compound is obtained in an about 76% yield.

### Claim 15 (depends on 8)

The method of making the 4,5-bis(4-chlorophenyl)-2-phenyl-1H-imidazole compound of claim 8, wherein the 1,2-bis(4-chlorophenyl)ethane-1,2-dione, benzaldehyde, and ammonium acetate are added in an about 1:1:1 molar ratio.