3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid as an antimicrobial compound
An 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound, its synthesis, and its use as an antimicrobial agent.
1. A 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound having the formula I:
2. The 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 1 , wherein the compound is obtained as a yellow solid.
3. The 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 1 , wherein the compound has a melting point of about 177° C. to about 178° C.
4. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 1 and a pharmaceutically acceptable carrier.
5. A method of treating a microbial infection caused by one or more gram positive bacteria, one or more gram negative bacteria, one or more fungi, or a combination thereof in a patient, the method comprising administering to a patient in need thereof a therapeutically effective amount of the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 1 .
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 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 1 , the method comprising:
mixing 5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol, 3-chloropropanoic acid, and sodium ethoxide in 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 filtration and recrystallization using ethanol; and
obtaining the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound.
10. The method of making the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 9 , wherein the irradiating step takes place in a sonicator for about 3 hours.
11. The method of making the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 9 , wherein the irradiating step is conducted at about 50° C.
12. The method of making the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic 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 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 9 , wherein the 5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol, the 3-chloropropanoic acid acid, and the sodium ethoxide are added in about a 1:1:4 molar ratio.
14. The method of making the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 9 , wherein the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound is obtained in a yield of about 73%.
15. The method of making the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound of claim 9 , wherein the 3-(5-(3-fluorophenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)propanoic acid compound is obtained as a yellow solid.