title: Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII.
abstract: By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. Some novel acridine bis-sulfonamides 6a-l were then synthesized by the reaction between sulfonyl chlorides and the novel amino-acridine sulfonamides 5a and 5b, obtained by reduction of nitro-acridine sulfonamide derivatives 4a and 4b. The newly synthesized compounds were investigated as inhibitors of 4 human carbonic anhydrase isoforms (hCA, EC 4.2.1.1). Several of the compounds showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII.
authors.affiliation: Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.
authors.forename: İbrahim
authors.initials: İ
authors.lastname: Esirden
authors.affiliation: Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.
authors.forename: Ramazan
authors.initials: R
authors.lastname: Ulus
authors.affiliation: Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.
authors.forename: Burak
authors.initials: B
authors.lastname: Aday
authors.affiliation: Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, 50019 Sesto Fiorentino (Florence), Italy.
authors.forename: Muhammet
authors.initials: M
authors.lastname: Tanç
authors.affiliation: Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, 50019 Sesto Fiorentino (Florence), Italy. Electronic address: claudiu.supuran@unifi.it.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
authors.affiliation: Biochemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey. Electronic address: muharrem.kaya@dpu.edu.tr.
authors.forename: Muharrem
authors.initials: M
authors.lastname: Kaya
mesh_terms: D000951:Antigens, Neoplasm / Q000378:metabolism*; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors* / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000071231:Carbonic Anhydrase IX; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000951:Antigens, Neoplasm; D002257:Carbonic Anhydrase Inhibitors; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II; C089226:CA9 protein, human; D000071231:Carbonic Anhydrase IX; D002256:Carbonic Anhydrases; C477378:carbonic anhydrase XII
keywords: Acridine; Carbonic anhydrase; Enzyme inhibition; Isoforms CA I, II, IX and VII; Sulfonamide