# US 12,178,802 B1 · 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol as an antitumor and antimicrobial compound

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,178,802 B1
- Document ID: US12178802B1
- Status: Granted
- Kind: B1
- Application number: 18/412,765
- Filed: 2024-01-15
- Granted: 2024-12-31
- Earliest claimed: 2023-08-24
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Lateef Ahmed; Mai Mostafa Khalaf Ali; Antar Ahmed Abdelhamid Ahmed; Adel A. Marzouk
- Web page: https://patentgrep.com/patent/US12178802B1

## CPC

- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A compound 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound, its synthesis, and its use as an anticancer, anti-inflammatory, and/or antimicrobial agent.

## Claims

### Claim 1

A method of making a 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound, the method comprising:
adding benzil, 2-hydroxypyridine-3-carbaldehyde, ammonium acetate, and N,N-dimethyl-3-aminopropane to piperidinium hydrogen sulfate in an oil bath to obtain a reaction mixture;
heating the reaction mixture with stirring until reaction completion to obtain a crude product;
purifying the crude product by recrystallization using absolute ethyl alcohol; and
obtaining the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound.

### Claim 2 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein the oil bath is at a temperature of about 25° C. to about 35° C.

### Claim 3 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein heating is at a temperature of about 100° C.

### Claim 4 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein after reaction completion the reaction mixture is washed with water.

### Claim 5 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein the benzil, 6-hydroxypyridine-2-carbaldehyde, and ammonium acetate are added in an about 1:1:1 molar ratio.

### Claim 6 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein the benzil, 6-hydroxypyridine-2-carbaldehyde, ammonium acetate, N,N-dimethyl-3-aminopropane are added in an about 1:1:1:0.5 molar ratio.

### Claim 7 (depends on 1)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound of claim 1, wherein the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol compound is obtained in an about 88% yield.