Dihalogenated sulfanilamides and benzolamides are effective inhibitors of the three β-class carbonic anhydrases from Mycobacterium tuberculosis

Figures & data

Table 1.  Inhibition data of mycobacterial β-CA isoforms mtCA 1–3 with sulfonamides 1–10 and benzolamide BZA by a stopped-flow, CO₂ hydrase assay²⁵.

	1-3	4-10		BZA
Compound	R1	R2	KI (μM)*
			mtCA 1	mtCA 2	mtCA 3
1	H	Cl	0.29	0.45	0.17
2	F	Br	0.14	0.43	0.27
3	F	I	0.12	0.41	0.3
4	F	Cl	1.17	4.56	3.02
5	F	Br	0.94	4.31	3.19
6	F	I	1.22	4.49	2.79
7	Cl	Cl	1.26	4.14	2.66
8	Cl	Br	0.58	4.62	2.69
9	Cl	I	1.27	4.74	2.67
10	Br	Br	0.41	4.52	2.03
–	BZA (benzolamide)		0.81	0.46	0.34

^*Errors in the range of ± 10 % of the reported values, by a CO₂ hydrase assay method (from three different measurements).

Ilies MA, Vullo D, Pastorek J, Scozzafava A, Ilies M, Caproiu MT et al. Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. J Med Chem 2003;46:2187–2196.

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