Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects

Figures & data

Scheme 1 Synthesis of title compounds.

Figure 1.  SDS-PAGE analysis of CA isoenzymes. Standard enzymes: Lane-1 (hCA-I),3(BCA),5(hCA-II). Enzymes used here: Lane-2(hCA-I),4(BCA),6(hCA-II).

Figure 2.  I₅₀ graph which were obtained from in vitro studies for compound 18 on hydratase activity of hCA-II.

Figure 3.  K_İ graph which were obtained from in vitro studies for compound 18 on hCA-I.

Table I.  I₅₀ values which were obtained from in vitro studies for the compounds (1, 2, 18–23) on hydratase activity of hCA-I and II.

	I50 (nM)
Inhibitors	hCA-I	hCA-II
1	5.1	5
2	1.1	13
18	1.2	0.4
19	2.2	0.42
20	2	0.98
21	1.2	1.1
22	1.4	0.9
23	1.4	2

Table II.  I₅₀ values which were obtained from in vitro studies for the compounds (1, 2, 18–23) on esterase activity of hCA-I and II.

	I50 (nM)
Inhibitors	hCA-I	hCA-II
1	9	2
2	9	4.9
18	1.4	3
19	2.9	1.3
20	8	4.7
21	5.4	4.2
22	2.8	5.6
23	5.9	6

Table III.  K_i values which were obtained from in vitro studies for synthesized compounds (1, 2, 18–23) on esterase of carbonic anhydrase isoenzymes.

	Ki (M)
Inhibitors	hCA-I	hCA-II
1	5.7 × 10^− 4	0.82 × 10^− 4
2	6.1 × 10^− 4	2 × 10^− 4
18	1.4 × 10^− 4	3 × 10^− 4
19	8.2 × 10^− 5	2.6 × 10^− 4
20	3.9 × 10^− 4	3 × 10^− 4
21	6.2 × 10^− 4	8.2 × 10^− 4
22	1 × 10^− 4	5.3 × 10^− 4
23	1 × 10^− 4	2.9 × 10^− 4