A novel proton transfer salt of 2-amino-6-sulfamoylbenzothiazole and its metal complexes: the evaluation of their inhibition effects on human cytosolic carbonic anhydrases

Abstract

A novel proton transfer compound (SMHABT)+(HDPC)− (1) obtained from 2-amino-6-sulfamoylbenzothiazole (SMABT) and 2,6-pyridinedicarboxylic acid (H2DPC) and its Fe(III), Co(II), Ni(II) complexes (2–4), and Fe(II) complex of SMABT (5) have been prepared and characterized by spectroscopic techniques. Additionally, single crystal X-ray diffraction techniques were applied to complexes (2–4). All complexes (2–4) have distorted octahedral conformations and the structure of 5 might be proposed as octahedral according to spectral and analytical results. All compounds, including acetazolamide (AAZ) as the control compound, were also evaluated for their in vitro inhibition effects on human hCA I and hCA II for their hydratase and esterase activities. The synthesized compounds have remarkable inhibitory activities on hCA I and hCA II. Especially, the inhibition potentials of the salt and the metal complexes (1–5) are comparable with AAZ. Inhibition data have been analyzed by using a one-way analysis of variance for multiple comparisons (p < .0001).

Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides

“…White solid, 80% yield; δ H (400 MHz, DMSO-d 6 ) 7.23 (2H, s, exchange with D 2 O, SO 2 N H 2 ), 7.45 (1H, d, J 8.4), 7.69 (1H, dd, J 8.4, 1.8), 7.89 (2H, s, exchange with D 2 O, N H 2 ), 8.15 (1H, d, J 1.8); δ C (100 MHz, DMSO-d 6 ) 118.0, 120.1, 124.6, 131.8, 137.2, 156.0, 170.3; m/z (ESI positive) 230.00 [M + H] + . Experimental in agreement with reported data 41 .…”

Synthesis and Characterization of Proton Transfer Salts of 2-Aminobenzothiazole Derivatives

“…2-Aminobenzotiyazol türevlerinin organik türevleri daha fazla çalışılmış olsa da proton transfer tuzu ve metal kompleksleri çok azdır. Literatürde 2-Aminobenzotiyazol türevlerinin 2,6-piridindikarboksilik asit [24][25][26][27][28][29][30], pikrik asit, süksinik asit, formik asit, p-klorofenoksiasetik asit, dikloroasetik asit trifloroasetik asit, stearik asit ve palmitik asit ile proton transfer tuzu ve metal kompleksleri vardır [31][32][33][34][35][36][37].…”