Corrigendum

Since the online publication of the following paper the authors have notified the publisher of an error in Table 1, Table 2 & Table 3.

Journal of Enzyme Inhibition and Medicinal Chemistry, iFirst article, 2008; 1–14DOI: 10.1080/14756360802188404

Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents

The Correct tables are as follows:

Table I.  Physical data of compounds 3-9.

Comp. No.	R	Yield %	M.P (^oC) Cryst. Solvent	Mol. Formula (Mol. wt.)	Comp. No.	R	Yield %	M.P (^oC) Cryst. Solvent	Mol. Formula (Mol. wt.)
3a	H	89	247-248 (DMF/H2O)(8:1)	C14H15N3O2S (289.36)	6d	Cl	74	240-241 (EtOH)	C19H18ClN5O3S (431.90)
3b	CH3	85	224-226 (Ethanol)	C15H17N3O2S (303.39)	6e	NO2	75	243-244 (EtOH)	C19H18N6O5S (442.46)
3c	Br	83	210-212 (Ethanol)	C14H14BrN3O2S (368.25)	7a	H	90	227-228 (EtOH)	C16H14N4O3S (342.38)
3d	Cl	87	221-222 (DMF/H2O) (8:1)	C14H14ClN3O2S (323.80)	7b	CH3	89	220-221 (MeOH)	C17H16N4O3S.1/2H2O (365.41)
3e	NO2	89	254-255 (DMF/H2O) (8:1)	C14H14N4O4S (334.36)	7c	Br	89	240-242 (EtOH/H2O) (5:1)	C16H13BrN4O3S (421.27)
4a	H	87	162-163 (DMF/H2O) (8:1)	C19H18N4O3S (382.44)	7d	Cl	88	230-232 (EtOH/H2O) (5:1)	C16H13ClN4O3S (376.82)
4b	CH3	86	129-130 (EtOH)	C20H20N4O3S (396.47)	7e	NO2	89	237-238 (EtOH)	C16H13N5O5S (387.38)
4c	Br	84	214-215 (EtOH)	C19H17BrN4O3S (461.34)	8a	H	85	190-191 (MeOH)	C19H17N5O2S (379.44)
4d	Cl	85	210-212 (EtOH)	C19H17ClN4O3S (416.89)	8b	CH3	84	236-237 (MeOH)	C20H19N5O2S (393.47)
4e	NO2	81	190-191^oC (DMF/H2O) (8:1)	C19H17N5O5S.H2O (445.46)	8c	Br	83	257-258 (EtOH)	C19H16BrN5O2S (458.34)
5a	H	75	182-183 (EtOH)	C16H13N3O3S (327.36)	8d	Cl	82	270-272 (EtOH)	C19H16ClN5O2S (413.89)
5b	CH3	73	170-171 (EtOH)	C17H15N3O3S (341.39)	8e	NO2	86	235-236 (DMF/H2O) (8:1)	C19H16N6O4S (424.44)
5c	Br	71	166-167 (EtOH)	C16H12BrN3O3S (406.26)	9a	H	89	219-220 (EtOH)	C16H12N4O2S.1/2H2O (333.37)
5d	Cl	70	162-163 (EtOH)	C16H12ClN3O3S.1/2H2O (370.82)	9b	CH3	88	200-202 (EtOH)	C17H14N4O2S.1/2H2O (347.40)
5e	NO2	65	210-212 (EtOH)	C16H12N4O5S (372.36)	9c	Br	90	252-253 (EtOH)	C16H11BrN4O2S (403.26)
6a	H	77	220-221^oC (EtOH)	C19H19N5O3S (397.46)	9d	Cl	89	244-245 (EtOH)	C16H11ClN4O2S (358.81)
6b	CH3	75	218-219 (EtOH/H2O) (5:1)	C20H21N5O3S (411.48)	9e	NO2	90	260-261 (DMF/H2O) (8:1)	C16H11N5O4S (369.36)
6c	Br	75	212-213^oC (EtOH)	C19H18BrN5O3S (476.36)

Table II.  IR and ¹H-NMR spectra of compounds 3-9.

Comp. No.	IR (KBr, cm^− 1)	^1H-NMR (DMSO-d6)
3a	3362, 3335, 3266(NH2, NH), 1595 (C = N), 1342, 1147 (SO2)	2.29 (s, 3H, CH3), 7.08 (s, 2H, NH2, D2O exchangeable), 7.30-7.43 (m, 5H, phenyl-H), 7.66, 7.82 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.73 (s, 1H, NH, D2O exchangeable).
3b	3360, 3333, 3264 (NH2, NH), 1596, (C = N), 1340, 1146 (SO2)	2.27 (s, 3H, tolyl CH3), 2.33 (s, 3H, CH3), 7.07 (s, 2H, NH2, D2O exchangeable), 7.21, 7.31 (2d, J = 8.0 Hz, 4H, tolyl C3,5-H & C2,6-H), 7.66, 7.71 (2d, J = 8.8 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.67 (s, 1H, NH, D2O exchangeable).
3c	3333, 3305, 3262 (NH2, NH), 1599 (C = N), 1339, 1151 (SO2)	2.28 (s, 3H, CH3), 7.10 (s, 2H, NH2, D2O exchangeable), 7.32, 7.58, 7.68, 7.76 (4d, J = 8.07 Hz, 8H, bromophenyl-H, benzenesulfonamide-H), 9.80 (s, 1H, NH, D2O exchangeable).
3d	3335, 3305, 3193, (NH2, NH), 1598 (C = N), 1339, 1151 (SO2)	2.28 (s, 3H, CH3), 7.09 (s, 2H, NH2, D2O exchangeable), 7.33, 7.45 (2d, J = 8.0 Hz, 4H, chlorophenyl-H), 7.68, 7.83 (2d, J = 8.8 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.81 (s, 1H, NH, D2O exchangeable).
3e	3303, 3246, 3111 (NH2, NH), 1594 (C = N), 1344, 1148 (SO2)	2.35 (s, 3H, CH3), 7.13 (s, 2H, NH2, D2O exchangeable), 7.40, 7.71, 8.07, 8.23 (4d, J = 8.8 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H), 10.08 (s, 1H, NH, D2O exchangeable).
4a	1679 (C = O), 1627, 1596 (C = N), 1338, 1147 (SO2).	2.92, 3.15 (2s, 6H, -N(CH3)2), 7.48-7.53 (m, 3H, phenyl C3,4,5-H), 7.90-7.97 (m, 4H, phenyl C2,6-H & benzenesulfonamide C3,5-H), 8.15 (d, J = 8.7 Hz, 2H, benzenesulfonamide C2,6-H), 8.25 (s, 1H, N = CH), 9.41 (s, 1H, pyrazole C5-H), 9.99 (s, 1H, CHO).
4b	1678 (C = O), 1627, 1595 (C = N), 1341, 1147 (SO2).	2.37 (s, 3H, tolyl CH3), 2.92, 3.15 (2s, 6H, N(CH3)2), 7.31, 7.80 (2d, J = 8.0 Hz, 4H, tolyl C3,5-H & C2,6-H), 7.94, 8.12 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.25 (s, 1H, N = CH), 9.38 (s, 1H, pyrazole C5-H), 9.97 (s, 1H, CHO).
4c	1690 (C = O); 1630, 1593 (C = N); 1339, 1150 (SO2).	2.92, 3.16 (2s, 6H, -N(CH3)2), 7.72 (d, J = 8.7 Hz, 2H, bromophenyl C3,5-H), 7.89-7.97 (m, 4H, bromophenyl C2,6-H & benzenesulfonamide C3,5-H), 8.13 (d, J = 9.0 Hz, 2H, benzenesulfonamide C2,6-H), 8.25 (s, 1H, N = CH), 9.45 (s, 1H, pyrazole C5-H), 9.98 (s, 1H, CHO).
4d	1690 (C = O); 1636, 1593 (C = N); 1337, 1150 (SO2).	2.92, 3.16 (2s, 6H, N(CH3)2), 7.58, 7.94 (2d, J = 8.4 Hz, 4H, chlorophenyl-H), 8.00, 8.14 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.26 (s, 1H, N = CH), 9.44 (s, 1H, pyrazole C5-H), 9.98 (s, 1H, CHO).
4e	1688 (C = O); 1627, 1595 (C = N); 1344, 1149 (SO2).	2.93, 3.16 (2s, 6H, N(CH3)2), 7.96, 8.16, 8.25, 8.28 (4d, J = 8.7 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H),8.29 (s, 1H, CH = N), 9.52 (s, 1H, pyrazole C5-H), 10.02 (s, 1H, CHO).
5a	3347, 3236 (NH2); 1665 (C = O); 1596 (C = N); 1339, 1158 (SO2).	7.47 (s, 2H, NH2, D2O exchangeable), 7.48-7.54 (m, 3H, phenyl C3,4,5-H), 7.92-7.96 (m, 2H, phenyl C2,6-H), 8.00, 8.21 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.43 (s, 1H, pyrazole C5-H), 10.00 (s, 1H, CHO).
5b	3351, 3234 (NH2); 1661 (C = O); 1595 (C = N); 1346, 1163 (SO2).	2.38 (s, 3H, CH3), 7.33 (d, J = 7.95 Hz, 2H, tolyl C3,5-H), 7.47 (s, 2H, NH2, D2O exchangeable), 7.83 (d, J = 7.95 Hz, 2H, tolyl C2,6-H), 8.00, 8.19 (2d, J = 8.55 Hz, 2H, benzenesulfonamide C3,5-H & C2,6-H), 9.40 (s, 1H, pyrazole C5-H), 9.99 (s, 1H, CHO).
5c	3344, 3254 (NH2); 1681 (C = O); 1596 (C = N); 1336, 1165 (SO2).	7.48 (s, 2H, NH2, D2O exchangeable), 7.73, 7.93, 8.00, 8.20 (4d, J = 8.7 Hz, 8H, bromophenyl-H & benzenesulfonamide-H), 9.46 (s, 1H, pyrazole C5-H), 9.99 (s, 1H, CHO).
5d	3347, 3260 (NH2); 1680 (C = O); 1596 (C = N); 1335, 1161 (SO2).	7.47 (s, 2H, NH2, D2O exchangeable), 7.72, 7.92, 8.00, 8.18 (4d, J = 8.7 Hz, 8H, chlorophenyl-H & benzenesulfonamide-H), 9.45 (s, 1H, pyrazole C5-H), 9.97 (s, 1H, CHO).
5e	3350, 3263 (NH2); 1681 (C = O); 1596 (C = N); 1344, 1166 (SO2).	7.50 (s, 2H, NH2, D2O exchangeable), 8.01 (d, J = 8.7 Hz, 2H, nitrophenyl C2,6-H), 8.20, 8.26 (2d, J = 9.0 Hz,4H, benzenesulfonamide C3,5-H & C2,6-H), 8.36 (d, J = 8.7 Hz, 2H, nitrophenyl C3,5-H), 9.52 (s, 1H, pyrazole C5-H), 10.03 (s, 1H, CHO).
6a	3373 (OH); 1643, 1595 (C = N); 1334, 1161 (SO2).	2.91, 3.15 (2s, 6H, -N(CH3)2), 7.43 (s, 1H, CH = N), 7.49-7.54 (m, 3H, phenyl C3,4,5-H), 7.66 (m, 2H, phenyl C2,6-H), 7.89, 8.10 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.23 (s, 1H, N = CH), 9.22 (s, 1H, pyrazole C5-H), 11.86 (s, 1H, OH, D2O exchangeable).
6b	3244 (OH); 1628, 1595 (C = N); 1340, 1161 (SO2).	2.35 (s, 3H, tolyl CH3), 2.90, 3.13 (2s, 6H, N(CH3)2), 7.31 (d, J = 8.0 Hz, 2H, tolyl C3,5-H), 7.40 (s, 1H, CH = N), 7.53 (d, J = 8.0 Hz, 2H, tolyl C2,6-H), 7.87, 8.07 (2d, J = 9.1 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.23 (s, 1H, N = CH), 9.20 (s, 1H, pyrazole C5-H), 11.84 (s, 1H, OH, D2O exchangeable).
6c	3391 (OH); 1631, 1595 (C = N); 1344, 1152 (SO2).	2.92, 3.15 (2s, 6H, N(CH3)2), 7.44 (s, 1H, CH = N), 7.58, 7.71 (2d, J = 8.56 Hz, 4H, bromophenyl-H), 7.96, 8.16 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.23 (s, 1H, N = CH), 9.26 (s, 1H, pyrazole C5-H), 11.91 (s, 1H, OH, D2O exchangeable).
6d	3238 (OH); 1627, 1596 (C = N); 1340, 1161 (SO2).	2.89, 3.13 (2s, 6H, N(CH3)2), 7.41 (s, 1H, CH = N), 7.56, 7.67 (2d, J = 8.3 Hz, 4H, chlorophenyl-H), 7.86, 8.07 (2d, J = 8.6 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.22 (s, 1H, N = CH), 9.21 (s, 1H, pyrazole C5-H), 11.94 (s, 1H, OH, D2O exchangeable).
6e	3248 (OH); 1629, 1596 (C = N); 1343, 1149 (SO2).	2.92, 3.15 (2s, 6H, N(CH3)2), 7.53 (s, 1H, CH = N), 7.93, 8.03, 8.13, 8.35 (4d, J = 8.8 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H), 8.25 (s, 1H, N = CH), 9.0 (s, 1H, pyrazole C5-H), 11.25 (s, 1H, OH, D2O exchangeable).
7a	3350, 3255, 3113 (NH2, OH), 1595 (C = N), 1334, 1161 (SO2).	7.42 (s, 3H, CH = N & NH2), 7.46-7.70 (m, 5H, phenyl-H), 7.95, 8.16 (2d, J = 8.7 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.26 (s, 1H, pyrazole C5-H), 11.88 (s, 1H, OH, D2O exchangeable).
7b	3335, 3256, 3115 (NH2, OH), 1595 (C = N), 1336, 1160 (SO2).	2.36 (s, 3H, CH3), 7.34 (d, J = 7.8 Hz, 2H, tolyl C3,5-H), 7.43 (s, 3H, CH = N & NH2), 7.56 (d, J = 7.8 Hz, tolyl C2,6-H), 7.95, 8.16 (2d, J = 9.0 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.24 (s, 1H, pyrazole C5-H), 11.86 (s, 1H, OH, D2O exchangeable).
7c	3352, 3250, 3186 (NH2, OH), 1596 (C = N), 1340; 1162 (SO2).	7.46 (s, 2H, NH2, D2O exchangeable), 7.48 (s, 1H, CH = N), 7.63, 7.71, 7.94, 8.15 (4d, J = 8.4 Hz, 8H, bromophenyl-H & benzenesulfonamide-H), 9.25 (s, 1H, pyrazole C5-H), 11.95 (s, 1H, OH, D2O exchangeable).
7d	3353, 3254, 3188 (NH2, OH), 1595 (C = N), 1342, 1158 (SO2).	7.43 (s, 1H, CH = N), 7.44 (s, 2H, NH2, D2O exchangeable), 7.57, 7.69 (2d, J = 8.4 Hz, 4H, chlorophenyl-H), 7.94, 8.14 (2d, J = 8.7 Hz, 4H, zenesulfonamide C3,5-H & C2,6-H), ben9.25 (s, 1H, pyrazole C5-H), 11.91 (s, 1H, OH, D2O exchangeable).
7e	3330, 3250, 3150 (NH2, OH), 1596 (C = N), 1340, 1162 (SO2).	7.48 (s, 2H, NH2, D2O exchangeable), 7.55 (s, 1H, CH = N), 7.98, 8.02, 8.20, 8.40 (4d, J = 8.8 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H), 9.33 (s, 1H, pyrazole C5-H), 12.01 (s, 1H, OH, D2O exchangeable).
8a	2230 (C = N), 1631, 1592 (C = N), 1338, 1152 (SO2).	2.93, 3.16 (2s, 6H, N(CH3)2), 7.54-7.62 (m, 3H, phenyl C3,4,5-H), 7.97-8.01 (m, 4H, phenyl C2,6-H & benzenesulfonamide C3,5-H), 8.10 (d, J = 8.8 Hz, 2H, benzenesulfonamide C2,6-H), 8.27 (s, 1H, N = CH), 9.56 (s, 1H, pyrazole C5-H).
8b	2232 (C = N), 1635, 1592 (C = N), 1340, 1152 (SO2).	2.39 (s, 3H, tolyl CH3), 2.93, 3.20 (2s, 6H, N(CH3)2), 7.39, 7.87, 7.97, 8.09 (4d, J = 8.0 Hz, 8H, tolyl-H, benzenesulfonamide-H), 8.27 (s, 1H, N = CH), 9.53 (s, 1H, pyrazole C5-H).
8c	2233 (C = N), 1636, 1594 (C = N), 1339, 1153 (SO2).	2.93, 3.16 (2s, 6H, N(CH3)2), 7.82, 7.94 (2d, J = 8.0 Hz, 4H, bromophenyl-H), 7.97, 8.10 (2d, J = 8.8 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 8.27 (s, 1H, N = CH), 9.57 (s, 1H, pyrazole C5-H).
8d	2233 (C ≡ N), 1637, 1593 (C = N), 1340, 1152 (SO2).	2.93, 3.16 (2s, 6H, N(CH3)2), 7.67, 7.96, 8.00, 8.10 (4d, J = 8.8 Hz, 8H, chlorophenyl-H & benzenesulfonamide-H), 8.27 (s, 1H, N = CH), 9.57 (s, 1H, pyrazole C5-H).
8e	2233 (C = N), 1631, 1595 (C = N), 1341, 1146 (SO2).	2.90, 3.14 (2s, 6H, N(CH3)2), 7.96, 8.08, 8.21, 8.41 (4d, J = 9.0 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H), 8.24 (s, 1H, N = CH), 9.59 (s, 1H, pyrazole C5-H).
9a	3372, 3279 (NH2), 2225 (C = N), 1594 (C = N), 1338, 1157 (SO2).	7.51 (s, 2H, NH2, D2O exchangeable), 7.54-7.62 (m, 3H, phenyl C3,4,5-H), 7.98-8.03 (m, 4H, phenyl C2,6-H & benzenesulfonamide C3,5-H), 8.16 (d, J = 8.8 Hz, 2H, benzenesulfonamide C2,6-H), 9.57 (s, 1H, pyrazole C5-H).
9b	3347, 3258 (NH2), 2227 (C = N), 1596 (C = N), 1330, 1164 (SO2).	2.39 (s, 3H, CH3), 7.40 (d, J = 8.0 Hz, 2H, tolyl C3,5-H), 7.51 (s, 2H, NH2, D2O exchangeable), 7.89 (d, J = 8.0 Hz, 2H, tolyl C2,6-H), 8.01, 8.15 (2d, J = 8.8 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.54 (s, 1H, pyrazole C5-H).
9c	3325, 3231 (NH2), 2228 (C = N), 1595 (C = N), 1337, 1157 (SO2).	7.50 (s, 2H, NH2, D2O exchangeable), 7.77, 7.91 (2d, J = 8.4 Hz, 4H, bromophenyl-H), 8.00, 8.08 (2d, J = 9 Hz, 4H, benzenesulfonamide C3,5-H & C2,6-H), 9.53 (s, 1H, pyrazole C5-H).
9d	3271, 3209 (NH2); 2234 (C = N), 1595 (C = N), 1343, 1166 (SO2).	7.52 (s, 2H, NH2, D2O exchangeable), 7.68 (d, J = 8.8 Hz, 2H, chlorophenyl C3,5-H), 7.98-8.03 (m, 4H, chlorophenyl C2,6-H & benzenesulfonamide C3,5-H), 8.15 (d, J = 8.8 Hz, 2H, benzenesulfonamide C2,6-H), 9.58 (s, 1H, pyrazole C5-H).
9e	3262, 3227 (NH2); 2232 (C = N), 1596 (C = N), 1345, 1163 (SO2).	7.47 (s, 2H, NH2, D2O exchangeable), 8.12, 8.21, 8.25, 8.45 (4d, J = 8.8 Hz, 8H, nitrophenyl-H & benzenesulfonamide-H), 9.67 (s, 1H, pyrazole C5-H).

Table III.  The anti-inflammatory activity (ED₅₀, μmol/cotton pellet)^a and ulcerogenic activity^a.

Test Compound	ED50 (μmol)	% Ulceration
Indomethacin	9.68 ± 0.27	100
Celecoxib	16.74 ± 0.22	0.0
6a	12.36 ± 0.28	0.0
6b	10.64 ± 0.32	10
6c	10.72 ± 0.18	10
6d	11.96 ± 0.27	0.0
6e	11.76 ± 0.43	0.0
7a	9.46 ± 0.28	0.0
7b	9.38 ± 0.36	0.0
7c	11.06 ± 0.45	10
7d	10.98 ± 0.26	10
7e	10.34 ± 0.34	0.0
8a	10.96 ± 0.52	0.0
8b	11.36 ± 0.26	0.0
8c	11.58 ± 0.33	10
8d	13.28 ± 0.44	10
8e	10.34 ± 0.42	0.0
9a	8.58 ± 0.16	0.0
9b	8.94 ± 0.25	0.0
9c	10.88 ± 0.24	0.0
9d	11.06 ± 0.27	20
9e	13.82 ± 0.35	10

^a All data are significantly different from control (P < 0.001).