title: Synthesis of biologically active O-substituted derivatives of 1-[(3, 5-dichloro-2-hydroxyphenyl)sulfonyl]piperidine.
abstract: In the present work, a series of 2-O-substituted derivatives of 1-[(3,5-dichloro-2-hydroxy phenyl) sulfonyl]piperidine (5a-j) were synthesized. These derivatives were geared up by the coupling of 3,5-dichloro-2-hydroxy benzenesulfonyl chloride (1) with piperidine (2) under dynamic pH control in aqueous media to form parent compound 1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidine (3), followed by the substitution at oxygen atom with different electrophiles (4a-j) in the presence of sodium hydride (NaH) and dimethyl formamide (DMF) to give a series of O-substituted derivatives of sulfonamides bearing piperidine nucleus 5a-j. The synthesized O-substituted sulfonamides were spectrally characterized. The bioactivity of all the synthesized compounds were evaluated against lipoxygenase (LOX), acetylcholinesterae (AChE) and butyrylcholinesterase (BChE) enzymes and found to be having talented activity against butyrylcholinesterase enzyme.
authors.affiliation: Department of Chemistry, Government College University, Lahore, Pakistan.
authors.forename: Hira
authors.initials: H
authors.lastname: Khalid
authors.forename: Azizur
authors.initials: A
authors.lastname: Rehman
authors.forename: Muhammad Athar
authors.initials: MA
authors.lastname: Abbasi
authors.forename: Khalid Mohammad
authors.initials: KM
authors.lastname: Khan
authors.forename: Muhammad
authors.initials: M
authors.lastname: Ashraf
authors.forename: Irshad
authors.initials: I
authors.lastname: Ahmad
authors.forename: Syeda Abida
authors.initials: SA
authors.lastname: Ejaz
mesh_terms: D002091:Butyrylcholinesterase / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017670:Sodium Compounds / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D002800:Cholinesterase Inhibitors; D016859:Lipoxygenase Inhibitors; D010880:Piperidines; D017670:Sodium Compounds; C524957:sodium hydride; D008084:Lipoxygenase; D002091:Butyrylcholinesterase; D010100:Oxygen