Supporting Information
Discovery of low nanomolar and subnanomolar inhibitors of the mycobacterial β-
carbonic anhydrases Rv1284 and Rv3273
Ö. Güzel, A. Maresca, A. Scozzafava, A. Salman, A.T. Balaban, C.T. Supuran
b *
1-({[5-(Aminosulfonyl)-3-(2-methylphenyl)-1H-indol-2-yl]carbonyl}amino)-2,4,6
trimethylpyridinium perchlorate 4. Yield 48%; m.p. > 300 C (dec.);
1
H-NMR (DMSO-d
6
,
300MHz) δ (ppm): 2.12 (3H, s, phenyl 2-CH
3
), 2.44 (3H, s, pyridinium 4-CH
3
), 2.52 (6H, s,
pyridinium 2,6-(CH
3
)
2
), 7.12 (2H, s, SO
2
NH
2
), 7.19-7.36 (4H, m, Ar-H), 7.50-7.72 (6H, m,
Ar-H and CONH), 11.90 (1H, s, indole NH); LC/MS: m/z 450 (M+H)
+
. Elem. anal. (C, H, N,
S).
1-({[5-(Aminosulfonyl)-3-(3-methylphenyl)-1H-indol-2-yl]carbonyl}amino)-2,4,6
trimethylpyridinium perchlorate 5. Yield 43%; m.p. > 300 C (dec.);
1
H-NMR (DMSO-d
6
,
300MHz) δ (ppm): 2.40 (3H, s, phenyl 3-CH
3
), 2.52 (9H, s, pyridinium 2,4,6-(CH
3
)
3
), 7.26
(2H, s, SO
2
NH
2
), 7.42 (4H, s, Ar-H), 7.62-7.94 (5H, m, Ar-H), 8.04 (1H, s, CONH), 12.40
(1H, s, indole NH); LC/MS: m/z 450 (M+H)
+
. Elem. anal. (C, H, N, S).
1-({[5-(Aminosulfonyl)-3-(4-methylphenyl)-1H-indol-2-yl]carbonyl}amino)-2,4,6
trimethylpyridinium perchlorate 6. Yield 54%; m.p. > 300 C (dec.);
1
H-NMR (DMSO-d
6
,
300MHz) δ (ppm): 2.39 (3H, s, phenyl 4-CH
3
), 2.59 (9H, s, pyridinium 2,4,6-(CH
3
)
3
), 7.19
(2H, s, SO
2
NH
2
), 7.33 (2H, d, Ar-H), 7.50 (2H, d, Ar-H), 7.64-7.94 (5H, m, Ar-H), 8.00 (1H,
s, CONH), 12.20 (1H, s, indole NH); LC/MS: m/z 450 (M+H)
+
. Elem. anal. (C, H, N, S).
1-({[5-(Aminosulfonyl)-3-(2-fluorophenyl)-1H-indol-2-yl]carbonyl}amino)-2,4,6
trimethylpyridinium perchlorate 7. Yield 42%; m.p. > 300 C (dec.);
1
H-NMR (DMSO-d
6
,
300MHz) δ (ppm): 2.53 (3H, s, pyridinium 4-CH
3
), 2.57 (6H, s, pyridinium 2,6-(CH
3
)
2
), 7.21
(2H, s, SO
2
NH
2
), 7.28-7.38 (3H, m, Ar-H), 7.46 (2H, s, Ar-H), 7.56 (2H, s, Ar-H), 7.77 (2H,
s, Ar-H), 7.88 (1H, s, CONH), 12.25 (1H, s, indole NH); LC/MS: m/z 454 (M+H)
+
. Elem.
anal. (C, H, N, S).