title: Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase.
abstract: A series of carbamate derivatives were synthesized and their carbonic anhydrase I and II isoenzymes and acetylcholinesterase enzyme (AChE) inhibitory effects were investigated. All carbamates were synthesized from the corresponding carboxylic acids via the Curtius reactions of the acids with diphenyl phosphoryl azide followed by addition of benzyl alcohol. The carbamates were determined to be very good inhibitors against for AChE and hCA I, and II isoenzymes. AChE inhibition was determined in the range 0.209-0.291 nM. On the other hand, tacrine, which is used in the treatment of Alzheimer's disease possessed lower inhibition effect (Ki: 0.398 nM). Also, hCA I and II isoenzymes were effectively inhibited by the carbamates, with inhibition constants (Ki) in the range of 4.49-5.61 nM for hCA I, and 4.94-7.66 nM for hCA II, respectively. Acetazolamide, which was clinically used carbonic anhydrase (CA) inhibitor demonstrated Ki values of 281.33 nM for hCA I and 9.07 nM for hCA II. The results clearly showed that AChE and both CA isoenzymes were effectively inhibited by carbamates at the low nanomolar levels.
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .
authors.forename: Süleyman
authors.initials: S
authors.lastname: Yılmaz
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .|b Department of Basic Science , Faculty of Science, Erzurum Technical University , Erzurum , Turkey .
authors.forename: Yusuf
authors.initials: Y
authors.lastname: Akbaba
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .|b Department of Basic Science , Faculty of Science, Erzurum Technical University , Erzurum , Turkey .
authors.forename: Bünyamin
authors.initials: B
authors.lastname: Özgeriş
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .
authors.forename: Leyla Polat
authors.initials: LP
authors.lastname: Köse
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .
authors.forename: Süleyman
authors.initials: S
authors.lastname: Göksu
authors.affiliation: a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey .|c Department of Zoology , College of Science, King Saud University , Riyadh , Saudi Arabia .
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gülçin
authors.affiliation: c Department of Zoology , College of Science, King Saud University , Riyadh , Saudi Arabia .
authors.forename: Saleh H
authors.initials: SH
authors.lastname: Alwasel
authors.affiliation: d Dipartimento di Chimica Ugo Schiff, Universita Degli Studi di Firenze , Sesto Fiorentino , Firenze , Italy , and.|e Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences, Universita Degli Studi di Firenze , Sesto Fiorentino , Florence , Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D002219:Carbamates; D002257:Carbonic Anhydrase Inhibitors; D002800:Cholinesterase Inhibitors; D000110:Acetylcholinesterase; D002256:Carbonic Anhydrases
keywords: Acetylcholinesterase; carbamates; carbonic anhydrase; enzyme inhibition; synthesis