Table 1.

TweCAδ, hCA I, and hCA II Inhibition Data with MTCs 1–15, DTCs 16–36, and acetazolamide (AAZ, 5-acetamido-1,3,4-thiadiazole-2-sulphonamide) as standard drug, by a stopped-flow CO₂ hydrase assay.

	RR1NCOS− Na+ (1–15)		RR1NCS2M (16–36)
			KI (nM)a
No.	R	R1	TweCAδ	hCA I	hCA II
1	n-Pr	n-Pr	806.7	>2000	46.7
2	Et	n-Bu	783.3	700	>2000
3	n-Bu	n-Bu	1142	909	>2000
4	i-Bu	i-Bu	>20,000	681	43.0
5	Me	CH2COOEt	>20,000	827	44.5
6		–(CH2CH2)–O–(CH2CH2)–	>20,000	569	>2000
7	H	–N(CH2CH2)N(CH3)CH2CH2–	487	>2000	35.0
8		– (CH2CH2)–NH-(CH2CH2)–	483	876	22.4
9		–(CH2CH2)-N(CH2CONHC6H11)–(CH2CH2)–	129	949	45.9
10	Me	CH2Ph	>20,000	>2000	>2000
11	H	CH2CH2Ph	997	>2000	43.7
12		HCH2CH2(3,4-di-MeO-C6H4)	67.7	891	26.7
13		– (CH2CH2)–N(3-Cl-C6H4)– (CH2CH2)–	1505	686	>2000
14		–(CH2CH2)–N(4-F-C6H4)–(CH2CH2)–	1498	895	46.8
15		–(CH2CH2)-N(4-CF3-C6H4)– (CH2CH2)–	1152	>2000	43.6
16	Me2N(CH2)2	H	8406	85.9	35.8
17	HO(CH2)3	H	8691	706	41.7
18	HO(CH2)4	H	7168	295	24.3
19	HO(CH2)5	H	8597	66.5	17.3
20		H	>20,000	494	48.7
21	(R)	H	>20,000	240	18.9
22	(S)	H	7995	615	65.9
23	–(CH2)5–	–	>20,000	252	30.1
24	–(CH2)3–CH(OH)CH2–	–	>20,000	428	60.7
25	–(CH2)4–CH(COONa)–	–	>20,000	485	80.1
26	–(CH2)3–CH(COONa)CH2–	–	8429	290	45.4
27	(R)–(CH2)3–CH(COONa)CH2–	–	93.6	496	80.5
28	(S) -(CH2)3–CH(COONa)CH2–	–	556	109	8.9
29	–(CH2)2–CH(COONa)(CH2)2–	–	8980	337	78.7
30	–(CH2)3-CH(NHAc)CH2–	–	783	910	47.9
31	–(CH2)3-CH(NHBoc)CH2–	–	9239	683	13.2
32	–CH(Me)CH2-O-(CH2)2–	–	>20,000	434	60.2
33	–CH(COONa)CH2-O– (CH2)2–	–	>20,000	84.7	78.5
34	–	–(CH2)2 N(CH2CONHC6H11)(CH2)2–	791	415	67.2
35	Ph(CH2)2	H	897	425	107
36	–	H2NO2SC6H4(CH2)2H	704	97.5	48.1
AAZ	–	–	83	250	12.1

^aMean ± standard error (from three different assays), by a stopped-flow technique (errors were in the range of ±5–10% of the reported values).