title: Synthesis of new sulfonamides as lipoxygenase inhibitors.
abstract: The present study describes a convenient method for the synthesis of new lipoxygenase inhibitors, 4-(toluene-4-sulfonylamino)-benzoic acids from p-amino benzoic acid. Reaction of p-amino benzoic acid with p-toluenesulfonyl chloride provided thirteen N- and O-alkylation products 4a-4m in moderate to good yields. Lipoxygenase inhibition of newly formed sulfonamide derivatives was investigated and some of these compounds 4m, 4g, 4e, 4f and 4j showed good lipoxygenase inhibitory activities with IC(50) values ranged between 15.8 ± 0.57 and 91.7 ± 0.61 μmol whilst all other compounds exhibited mild anti-lipoxygenase activities with IC(50) values ranged between 139.2 ± 0.75 and 232.1 ± 0.78 μmol. N-alkylated products were more active against the enzyme than O-alkylated or both N- and O-alkylated ones. All synthesized sulfonamides were recrystallized in chloroform to give these title compounds which were characterized using FTIR, (1)H NMR, (13)C NMR, elemental analysis and single crystal X-ray diffraction techniques.
authors.affiliation: Materials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan. gmustafa884@yahoo.com
authors.forename: Ghulam
authors.initials: G
authors.lastname: Mustafa
authors.forename: Islam Ullah
authors.initials: IU
authors.lastname: Khan
authors.forename: Muhammad
authors.initials: M
authors.lastname: Ashraf
authors.forename: Iftikhar
authors.initials: I
authors.lastname: Afzal
authors.forename: Sohail Anjum
authors.initials: SA
authors.lastname: Shahzad
authors.forename: Muhammad
authors.initials: M
authors.lastname: Shafiq
mesh_terms: D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D016859:Lipoxygenase Inhibitors; D013449:Sulfonamides; D001094:Arachidonate 5-Lipoxygenase