| Title |
Synthesis and biological evaluation of alkylated 2-mercaptoimidazoles bearing a benzenesulfonamide moiety |
| Authors |
Vainauskas, Valdas ; Grybaitė, Birutė ; Kavaliauskas, Povilas ; Mickevičius, Vytautas |
| Full Text |
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| Is Part of |
25th Tetrahedron Symposium, Bruges, Belgium, 1-4 July 2025.. [S.l.] : Elsevier. 2025, p. 1-2 |
| Abstract [eng] |
Benzenesulfonamides are widely explored due to their wide range of potential pharmaceutical uses as anticancer, antibacterial drugs [1]. As well as functionalized 2-mercaptoimidazoles which present potent anticancer activity [2]. In this present study, α-aminoketone 2 was obtained by reacting the primary amine 1 with bromoacetophenone, which in turn was reacted with potassium thiocyanate in the presence of hydrochloric acid to obtain 2-mercaptoimidazole 3. Compounds 4-13 were synthesized by alkylating 2-mercaptoimidazole 3 with a corresponding bromoacetophenones in methanol at reflux, using sodium bicarbonate as a weak base. Similarly, compound 14 was yielded by performing an alkylation with 4-nitrochlorobenzene in dimethylformamide using potassium hydroxide as a strong base, as well as potassium carbonate. Ester 15 was obtained by alkylating 2-mercaptoimidazole 3 with methyl bromoacetate in ethanol in presence of potassium carbonate and in turn was hydrolyzed with a sodium hydroxide solution to obtain carboxylic acid 16. Benzimidazoles 17, 18 were prepared by condensing corresponding benzenediamines with an ester in presence of hydrochloric acid. The structure of the synthesized compounds was characterized by spectral data (IR, NMR spectra, and elemental analysis). |
| Published |
[S.l.] : Elsevier |
| Type |
Conference paper |
| Language |
English |
| Publication date |
2025 |
