Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI

Figures & data

Figure 1.  Structures of the compounds.

Table 1.  hCA I, II and VI inhibition data with new sythetizedsynthesized sulfanilamine derivatives 1-12, sulfapyridine (13), sulfadiazine (14) and acetazolamide (15), by an esterase assay with 4-nitrophenylacetate as substrate.

KI (μM)
Compound	hCA I	hCA II	hCA VI
4-Methylbenzenesulfonamide (1)	22.120	0.715	18.970
4-Methyl-N-phenylbenzenesulfonamide (2)	210.3	14.3	13.44
4-Methyl-N-(naphthalen-2-yl)benzenesulfonamide (3)	322.0	0.612	42.39
4-Methyl-N-(2,4,6-trimethyl-phenyl)-benzenesulfonamide (4)	249.12	0.425	32.18
4-Methyl-N-o-tolyl-benzenesulfonamide (5)	148.27	0.407	29.58
N-(2-cyanophenyl)-4-methylbenzenesulfonamide (6)	18.24	0.213	8.430
4-Methyl-N-(2-nitrophenyl) benzenesulfonamide (7)	5.380	0.103	4.710
4-Methyl-N-p-tolyl-benzenesulfonamide (8)	50.02	1.015	24.28
N-(4-ethylphenyl)-4-methylbenzenesulfonamide (9)	448.2	0.977	26.53
N-(4-cyanophenyl)-4-methylbenzenesulfonamide (10)	1.480	0.120	1.230
4-Methyl-N-(4-nitrophenyl) benzenesulfonamide (11)	1.130	0.139	1.112
Benzenesulfonamide (12)	42.87	0.628	1.214
4-Amino-N-(pyridin-2-yl) benzenesulfonamide (Sulfapyridine) (13)	26.19	0.341	11.63
4-Amino-N-(pyrimidin-2-yl) benzenesulfonamide (Sulfadiazine) (14)	28.38	0.276	15.52
Acetazolamide (AZA) (15)	36.2	0.37	0.340