title: Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines.
abstract: Three 1-aminoindanes, four anilines and BnOH or t-BuOH were reacted with chlorosulfonyl isocyanate to give sulfamoyl carbamates. Pd-C catalysed hydrogenolysis reactions of carbamates or deprotection of the Boc group of the carbamates with CF3 CO2 H afforded seven novel sulfamides. Human carbonic anhydrase (hCA) isoenzymes I and II (hCA I and hCA II) were purified from fresh human blood erythrocytes with one-step affinity chromatography on Sepharose 4B-tyrosine-sulfanilamide. The inhibitory properties of the novel sulfamides on both isoenzymes were determined using the esterase activity with 4-nitrophenyl acetate (NPA) as substrate. The tested novel sulfamides derived from 1-aminoindanes and anilines effectively inhibited hCA I and II competitively in the nanomolar range. Among these compounds, the novel sulfamide derivative 17 showed the most potent inhibitory effect against hCA I (Ki : 153.88 nM), while sulfamide derivative 26 showed the highest inhibitory potential against hCA II (Ki : 117.80 nM).
authors.affiliation: Department of Basic Sciences, Faculty of Science, Erzurum Technical University, Erzurum, Turkey; Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey.
authors.forename: Yusuf
authors.initials: Y
authors.lastname: Akbaba
authors.forename: Enes
authors.initials: E
authors.lastname: Bastem
authors.forename: Fevzi
authors.initials: F
authors.lastname: Topal
authors.forename: Ilhami
authors.initials: I
authors.lastname: Gülçin
authors.forename: Ahmet
authors.initials: A
authors.lastname: Maraş
authors.forename: Süleyman
authors.initials: S
authors.lastname: Göksu
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D007189:Indans / Q000138:chemical synthesis* / Q000494:pharmacology*; D007527:Isoenzymes; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D002257:Carbonic Anhydrase Inhibitors; D007189:Indans; D007527:Isoenzymes; C016992:1-aminoindan; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II; C023650:aniline
keywords: Aminoindane; Aniline; Carbonic anhydrase; Enzyme inhibition; Sulfamide; Sulfamoyl carbamate