Ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate as an antimicrobial compound

1. An ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound having the formula I:

2. The ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 1 , wherein the compound has a melting point of about 156° C. to about 157° C.

3. The ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 1 , wherein the compound is a white solid.

4. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 1 and a pharmaceutically acceptable carrier.

5. A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 1 .

6. The method of treating the microbial infection of claim 5 , wherein the microbial infection is caused by one or more bacteria or fungi.

7. The method of treating the microbial infection of claim 6 , 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.

8. The method of treating the microbial infection of claim 7 , wherein the one or more gram positive bacteria are Bacillus cereus, Staphylococcus aureus , or a combination thereof.

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

10. The method of treating the microbial infection of claim 7 , wherein the one or more fungi are Aspergillus flavus, Chrysosporium keratinophilum , or a combination thereof.

11. A method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 1 , the method comprising:

adding a mixture of 5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol e-3-thiol, ethyl 4-bromobutyrate, and potassium carbonate to dimethylformamide (DMF) 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 ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound.

12. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the irradiating step takes place in a sonicator for about 45 minutes.

13. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the irradiating step is conducted at about 50° C.

14. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the purifying step comprises collecting the formed precipitate by filtration and washing the formed precipitate with distilled water.

15. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the 5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol, the ethyl 4-bromobutyrate, and the potassium carbonate are added in about a 1:1:1 molar ratio.

16. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the 3-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)propanoic acid compound is obtained in a yield of about 68%.

17. The method of making the ethyl 4-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)butanoate compound of claim 11 , wherein the 3-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)propanoic acid compound is obtained as a white solid.