Synthesis and Elucidation of the Chemical Structure of 2-(3-(4-substitutedphenyl)ureido)-N-phenylethane-1-sulfonamide Derivative
Project no. 28422 · Status: Kapanmış · 2023
Summary
<p>Many drugs with anticancer, antibacterial, and anticonvulsant effects comprimise the urea functional group in their structure. On the other hand, the research findings have substantiated the antimutagenic and chemoprotective properties of taurine. Additionally, our previous study revealed that taurine derivatives containing urea selectively inhibit cancer-associated carbonic anhydrase enzymes.</p><p>In this study, the synthesis of the final compound was conducted through a five-step process. In the initial step, a reaction between β-aminoethanesulfonic acid (taurine), phthalic anhydride, and potassium acetate in an acetic acid solution yielded β-phthalimidoethanesulfonic acid potassium salt. Subsequently, in the second step, the potassium salt was transformed into a sulfonyl chloride derivative. The third step involved a reaction between β-phthalimidoethanesulfonyl chloride and <em>p</em>-fluoroaniline. In the fourth step, the resulting phthalimidosulfonamide underwent refluxing with hydrazine hydrate in an ethanol solution. In the final step, the deprotected compound reacted with 4-methylphenyl isocyanate to obtain the final compound.</p><p>In order to confirm the structure of the compound, IR, 1H NMR, and 13C NMR spectral methods were utilized. As a result, the obtained data has demonstrated that the amino group of taurine can be derivatized as urea, thus enabling the design of projects that can lead to the production of a greater number of compounds.</p>