3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole as an antitumor and antimicrobial compound
A compound 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole, its synthesis, and its use as an anticancer and/or antimicrobial agent.
1. A method of making a 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound having the formula I:
the method comprising:
adding carbonyldiimidazole (CDI) to a solution of [5-methyl-2-(propan-2-yl)phenoxy]acetic acid in acetonitrile to obtain a reaction mixture;
adding N′-hydroxy-4-methoxybenzene-1-carboximidamide to the reaction mixture with stirring until reaction completion to obtain a precipitate; and
obtaining the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound.
2. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein the reaction mixture is stirred at room temperature for at least about 40 minutes before the adding of the N′-hydroxy-4-methoxybenzene-1-carboximidamide.
3. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein after the adding of the N-hydroxy-4-methoxybenzene-1-carboximidamide the reaction mixture is stirred for at least about 4 hours.
4. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein the precipitate is collected by filtration, washed several times with cold acetonitrile, dried, and recrystallized from the acetonitrile to obtain the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound.
5. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein the [5-methyl-2-(propan-2-yl)phenoxy]acetic acid and N′-hydroxy-4-methoxybenzene-1-carboximidamide are added in an about 1:1 molar ratio.
6. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein the [5--methyl-2-(propan-2-yl)phenoxy]acetic acid and CDI are added in an about 1:1.1 molar ratio.
7. The method of making the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound of claim 1 , wherein the 3-(4-methoxyphenyl)-5-{[5-methyl-2-(propan-2-yl)phenoxy]methyl}-1,2,4-oxadiazole compound is obtained in an about 89% yield.