Author/Authors :
Athar Abbasi, Muhammad Department of Chemistry - Government College University - Lahore-54000, Pakistan , Saeed, Amna Department of Chemistry - Government College University - Lahore-54000, Pakistan , ur-Rehman, Aziz Department of Chemistry - Government College University - Lahore-54000, Pakistan , Mohmmed Khan, Khalid HEJ Research Institute of Chemistry - International Center for Chemical and Biological Sciences - University of Karachi - Karachi-75270, Pakistan , Ashraf, Muhammad Department of Biochemistry and Biotechnology , Abida Ejaz, Syeda Department of Pharmacy - The Islamia University of Bahawalpur - Bahawalpur-63100, Pakistan
Abstract :
The present study reports the synthesis of a series N-substituted derivatives of brominated 2-phenitidine. First, the reaction of 2-phenitidine (1) with benzenesulfonyl chloride (2) in aqueous media yielded N-(2-ethoxyphenyl) benzenesulfonamide (3), which was then subjected to bromination with bromine in the presence of glacial acetic acid to give N-(4,5-dibromo- 2-ethoxyphenyl) benzenesulfonamide (4). Secondly, the product (4) on further treatment with alkyl/aryl halides (5a-l) in the presence of lithium hydride (LiH) produced twelve new derivatives of N-substituted sulfonamides (6a-l). These were characterized by 1H-NMR spectrum and screened against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) and were found to be valuable inhibitors of butyrylcholinesterase (BChE)
and acetylcholinesterase (AChE). Few of them were also active against LOX.
Keywords :
2-phenitidine , Sulfonamide , Bromination , Acetylcholinesterase , Bytyrylcholinesterase , Lipoxygenase , 1H-NMR