Exploring the Antibacterial Potential of Gabapentin Sulfonamide Analogues: Synthesis and Characterization

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Sajid Mahmood, Amimah Ashraf, Muhammad Waheed Rasheed, Zaheer Ahmad, Sajeela Fareed, Murat Cancan


Gabapentin Sulfonamide (2-(1-((4-methylphenylsulfonamido) methyl) cyclohexyl acetic acid) (3F) and their novel derivatives were synthesized. Gabapentin (1F) reacted with other reactant 4-methyl benzenesulphonyl chloride (C7H7ClO2S) (2F) in the presence of 10% Na2CO3 to synthesize the 2-(1-((4-methylphenylsulfonamido) methyl) cyclohexyl acetic acid (3F). This product (3F) was applied more for the preparation of derivatives of Gabapentin sulfonamide upon reaction with a series of organic alkyl/aralkyl halides by the application of base LiH and solvent DMF. Synthesized compounds were checked for their antibacterial activity by using various strains of bacteria including Escherichia Coli, Streptococcus faecalis, S. typhi, Staphylococcus aureus and Pseudomonas aeruginosa which showed excellent inhibited activity. Among the bacterial species, the compounds 5Fb and 5Fc have outstanding antibacterial activity for Pseudomomas aeruginosa (-) ATCC 14502 with zone of inhibition comparable with control drug (MIC 12.18). All the compounds were moderately to low active against the S. typhi. Structures of all the derivatives was confirmed by using UV- visible, IR, 1H-NMR and mass spectrometry.

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