Synthetic Development, Characterization and Antibacterial Activity of N-Substituted Derivatives of Procaine Sulfonamide

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Jalal Hatem Hussein Bayati, Sajid Mahmood, Amimah Ashraf, Muhammad Waheed Rasheed, Khursid Ayub, Amina Ashgar, Hassan Bilal, Iqra Yaseen


A new series of N-substituted Procaine sulfonamide derivatives (2-(diethylamino) ethyl 4-(phenylsulfonamido) benzoate) (3a) was synthesized and their antibacterial activity was assessed. The 2-(diethylamino) ethyl 4-(phenylsulfonamido) benzoate (3a) was produced by reacting benzene sulphonyl chloride (2a) with 2-(diethylamino) ethyl 4-aminobenzoate (1a) in the presence of 10% Na2CO3. The parent compound was used further for the synthesis of N- alkyl/aralkyl-(2-(diethylamino) ethyl 4-(phenylsulfonamido) benzoate) (5ac-ah) by the interaction of lithium hydride and aralkyl/alkyl halides (5c-h) in polar aprotic media. The synthesized compounds were subjected against different strains of bacteria containing Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, and Bacillus subtilis in comparison to conventional Ciprofloxacin to check their antibacterial activity and it was found that strong activity was shown by the compound 3a against Salmonella typhi. The derivative 5ac do not show inhibition activity against any bacteria except S. typhi. While compound 5ae was found to be a strong inhibitor of complete strains of bacteria, containing Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis with MIC values 9.52±1.00, 10.58±2.96, 11.75±3.42, 8.02±3.29 respectively but showed moderate inhibition against Salmonella typhi. EI-MS, IR and 1H-NMR spectral data was used to confirm the structures of the synthesized sulfonamide derivatives.

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