Carbonic anhydrase I, II, IV and IX inhibition with a series of 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives

Figures & data

Scheme 1. Synthesis of compounds 2–26.

Table 1. Inhibition data of hCA I, hCA II, hCA IV, hCA IX with compounds 2–26 reported here and the standard sulfonamide inhibitor acetazolamide (AAZ) by a stopped-flow CO₂ hydrase assay.

	KI (nm)
Cmp	hCA I	hCA II	hCA IV	hCA IX
2	8241.0	7467.6	>10,000	2133.3
3	6813.4	6966.7	>10,000	1461.0
4	3690.4	6852.2	>10,000	1051.8
5	>10,000	6379.1	>10,000	2234.6
6	3202.4	4437.9	>10,000	1688.2
7	>10,000	>10,000	>10,000	2420.3
8	>10,000	>10,000	>10,000	>10,000
9	>10,000	>10,000	>10,000	2267.5
10	>10,000	>10,000	>10,000	>10,000
11	>10,000	>10,000	>10,000	1158.3
12	>10,000	>10,000	>10,000	2489.6
13	>10,000	>10,000	>10,000	2105.0
14	>10,000	>10,000	>10,000	1373.1
15	>10,000	7883.8	>10,000	243.6
16	>10,000	5724.1	>10,000	>10,000
17	5328.9	4973.1	3801.4	2165.2
18	8749.6	5490.4	>10,000	1524.5
19	>10,000	>10,000	>10,000	2386.7
20	>10,000	3378.5	>10,000	1941.1
21	>10,000	>10,000	>10,000	>10,000
22	>10,000	>10,000	>10,000	2516.7
23	>10,000	>10,000	>10,000	1473.3
24	>10,000	>10,000	>10,000	292.8
25	>10,000	>10,000	>10,000	2758.6
26	>10,000	>10,000	>10,000	2658.3
AAZ	250	12	74	25

Errors were in the range of ±5–10% of the reported data, from three different assays.