title: The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes.
abstract: Phenolic mono Mannich bases [2-[4-hydroxy-3-(aminomethyl)benzylidene]-2,3-dihydro-1H-inden-1-one (8-15)] and bis Mannich bases [2-[4-hydroxy-3,5-bis(aminomethyl)benzylidene]-2, 3-dihydro-1H-inden-1-one (2-7)] were synthesized starting from 2-(4-hydroxybenzylidene)-2, 3-dihydro-inden-1-one (1). This study was designed in order to investigate the carbonic anhydrase (CA, EC 4.2.1.1) inhibitory properties of a library of compounds incorporating the phenol functional group. All prepared compounds showed a low inhibition percentages on both human (h) isoforms hCA I and hCA II compared to the reference sulfonamide acetazolamide. Mannich bases 2-15 had lower inhibition percentages than the compound 1 on hCA I and hCA II, except compound 14, which is a Mannich base derivative of dipropylamine, which had a similar inhibitory power as compound 1 on hCA II. All compounds synthesized 1-15 were 1.3-1.9 times more effective on hCA II comparing with the effectivenes of the compounds on hCA I.
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey and.|b Polo Scientifico, Laboratorio Di Chimica Bioinorganica, Universita Degli Studi Di Firenze , Sesto Fiorentino , Italy.
authors.forename: Cem
authors.initials: C
authors.lastname: Yamali
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey and.
authors.forename: Mehtap
authors.initials: M
authors.lastname: Tugrak
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey and.
authors.forename: Halise Inci
authors.initials: HI
authors.lastname: Gul
authors.affiliation: b Polo Scientifico, Laboratorio Di Chimica Bioinorganica, Universita Degli Studi Di Firenze , Sesto Fiorentino , Italy.
authors.forename: Muhammet
authors.initials: M
authors.lastname: Tanc
authors.affiliation: b Polo Scientifico, Laboratorio Di Chimica Bioinorganica, Universita Degli Studi Di Firenze , Sesto Fiorentino , Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D024401:Carbonic Anhydrase I / Q000187:drug effects*; D024402:Carbonic Anhydrase II / Q000187:drug effects*; D002257:Carbonic Anhydrase Inhibitors / Q000494:pharmacology*; D008352:Mannich Bases
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D008352:Mannich Bases; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Carbonic anhydrase; Mannich bases; indanone; phenol