Synthesis and Elucidation of the Chemical Structure of N-(2-(N-isopropylsulfamoyl)ethyl)-4-substituted benzamide Derivative
Project no. 28423 · Status: Kapanmış · 2023
Summary
<p>Taurine, also known as 2-aminoethanesulfonic acid, is not suitable for direct use as a drug substance due to its hydrophilic chemical nature. However, owing to its recognized efficacy in various biological pathways, researchers have conducted derivatization studies to modify its physicochemical properties, thereby enabling the preparation of novel taurine derivatives that hold promise for drug development. In line with this objective, the present study focused on the synthesis of a derivative named <em>N</em>-(2-(<em>N</em>-isopropylsulfamoyl)ethyl)-4-methylbenzamide, exhibiting distinct lipophilic and physicochemical properties. The objective of this study was to synthesize a compound by derivatizing the amino function of 2-aminoethanesulfonic acid as an amide and functionalizing the sulfonic acid group as a sulfonamide. The synthesis process involved five steps. In the first step, the reaction of 2-aminoethanesulfonic acid (taurine) with phthalic anhydride and potassium acetate in an acetic acid solution yielded the potassium salt of phthalimidoethanesulfonic acid. The second step involved the reaction of the phthalimidoethanesulfonic acid potassium salt with thionyl chloride and dimethyl formamide in a dichloromethane solution to obtain phthalimidoethane sulfonyl chloride. In the third step, the phthalimidoethanesulfonyl chloride compound was combined with isopropylamine in a dichloromethane solution, resulting in the formation of <em>N</em>-phenyl-2-phthalimidoethanesulfonamide. Subsequently, in the fourth step, <em>N</em>-isopropyl-2-phthalimidoethanesulfonamide was refluxed with hydrazine hydrate in ethanol, leading to the synthesis of 2-amino-<em>N</em>-isopropylethanesulfonamide. Finally, in the last step, 2-amino-<em>N</em>-isopropylethanesulfonamide hydrochloride was reacted with a solution of substituted benzoic acid and 1,1'-carbonylimidazole in acetonitrile, resulting in the final compound, <em>N</em>-(2-(<em>N</em>-isopropylsulfamoyl)ethyl)-4-methylbenzamide. Throughout the synthesis process, chromatographic methods were employed to monitor the reactions and obtain the pure final product. Furthermore, the structures of the final compounds were confirmed using IR, 1H NMR, and 13C NMR spectral methods.</p>