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).

The effects of some bromophenols on human carbonic anhydrase isoenzymes

“…In this study, both CA isoenzymes were purified by Sepharose-4B-L-tyrosine-sulfanilamide affinity chromatography in a single step [30][31][32] . The column material including Sepharose-4B-L-tyrosine-sulfanilamide was prepared according to a previous method [33][34][35] . Thus, homogenate solution acidity was adjusted and supernatant was transferred to the previously prepared Sepharose-4B-L-tyrosine-sulphanilamide affinity column [36][37][38] .…”

Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase

“…Human carbonic anhydrase isoenzymes (hCA I and II) and acetylcholine esterase (AChE) inhibition profile of carbamate derivatives (10)(11)(12)(13)(14)(15)(16) …”

“…Besides these drugs, the synthesis and biological evaluation of some carbamates have also been reported, e.g. anticancer 6 , HIV protease inhibition 7 , antimicrobial properties 8 , b-secretase inhibition 9 , CA and AChE inhibitory effects of carbamates and sulfamoylcarbamates have been investigated by different research groups [10][11][12] . Carbon dioxide (CO 2 ) and bicarbonate (HCO 3 À ) are essential components in living organism.…”

“…Therefore, here we focused on the synthesis of some novel carbamates (10)(11)(12). Then, we investigated AChE and hCA I, and II isoenzymes inhibitory properties of carbamates (10-16) for the first time.…”

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

“…a-CAs are among the most effective catalysts known in nature. The a-CAs are present in vertebrates, algae, protozoa, and cytoplasm compartment of green plants, as well as in some bacteria [27][28][29][30][31][32] . In humans, a-CAs are diffused in different tissues including the blood, kidneys, gastrointestinal tract, reproductive tract, the nervous central system, eyes, skin, lungs, etc.…”