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T. V. WANI ET AL.
2H, Ar–H), 7.16–7.10 (t, 2H, Ar–H), 6.93 (s, 2H, –SO2NH2–), (dd, 1H, Ha), 3.35 (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6):
6.66–6.63 (dd, 2H, Ar–H), 6.58–6.55 (t, 1H, Ar–NH), 5.62–5.56 (dd, d ¼ 171.95, 151.54, 147.39, 137.25, 134.4, 131.04, 129.16, 128.73,
1H, Hx), 4.42–4.35 (dd, 2H, –CH2–), 3.92–3.82 (dd, 1H, Ha), 128.4, 128.17, 127.72, 111.63, 44.44; IR (ATR, cmꢁ1): 3566 (OH str),
3.22–3.15 (dd, 1H, Ha); 13C-NMR (100 MHz, DMSO-d6): d ¼ 166.81, 3356, 3300 (N–H of NH2), 3259 (N–H str), 3072 (Ar C–H str), 2924
151.5, 142.96, 137.27, 133.84, 131.56, 131.09, 129.27, 128.74, (aliphatic C–H str), 1670 (C ¼ O str), 1147 (S ¼ O str), 729 (C–Cl str).
128.19, 127.7, 123.78, 111.62, 44.00; IR (ATR, cmꢁ1): 3362, 3300
(N–H of NH2), 3230 (N–H str), 3080 (Ar C–H str), 2846 (aliphatic
4-((2-(3-(4-Chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-
pyrazol-1-yl)-2-oxoethyl)amino)benzenesulphonamide (5h)
Yield: 70%; Rf: 0.61 (chloroform:methanol 9:1); M.P.: 170–173 ꢀC;
1H-NMR (300 MHz, DMSO-d6) d ppm: 7.88–7.82 (dd, 2H, Ar–H),
7.57–7.47 (m, 4H, Ar–H), 6.92 (s, 2H, SO2NH2), 6.87–6.80 (dd, 2H,
Ar–H), 6.71–6.65 (dd, 2H, Ar–H), 6.63–6.59 (t, 1H, Ar–NH), 5.82–5.77
C–H str), 1683 (C ¼ O str), 1155 (S ¼ O str), 736 (C–Cl str), 580
(C–Br str).
4-((2-(3-(4-Chlorophenyl)-5-(4-methylphenyl)-4,5-dihydro-1H-pyra-
zol-1-yl)-2-oxoethyl) amino)benzenesulphonamide (5d)
Yield: 70%; Rf: 0.57 (chloroform:methanol 9:1); M.P.: 151–154 ꢀC; (dd, 1H, Hx), 4.57–4.38 (dd, 2H, CH2), 4.02–3.92 (dd, 1H), 3.29–3.23
purity (HPLC): 100%; 1H-NMR (300 MHz, DMSO-d6)
d
ppm: (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6): d ¼ 167.18, 154.48,
7.85–7.80 (dd, 2H, Ar–H), 7.58–7.50 (m, 4H, Ar–H), 7.10 (s, 4H, 149.29, 148.54, 135.67, 134.81, 131.16, 130.29, 129.22, 128.92,
Ar–H), 6.89 (s, 2H, SO2NH2), 6.70–6.64 (dd, 2H, Ar–H), 6.45–6.42 (t, 127.66, 117.88, 112.31, 111.62, 110.01, 60.43, 56.02, 55.94; IR (ATR,
1H, Ar–NH), 5.57–5.53 (dd, 1H, Hx), 4.46–4.30 (dd, 2H, CH2), cmꢁ1): 3329 (N–H of NH2), 3209 (N–H str), 3087 (Ar C–H str), 2899
3.98–3.81 (dd, 1H, Ha), 3.18–3.12 (dd, 1H, Hb), 2.27 (s, 3H, Ar–CH3); (aliphatic C–H str), 1689 (C ¼ O str), 1153 (S ¼ O str), 732 (C–Cl str).
13C-NMR (100 MHz, DMSO-d6): d ¼ 167.02, 154.44, 151.4, 139.28,
137.23, 135.76, 131.16, 130.32, 129.19, 128.84, 128.14, 127.69,
125.89, 111.64, 60.41, 45.16, 42.2, 21.12; IR (ATR, cmꢁ1): 3362, 3294
4-((2-(3-(4-Chlorophenyl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-
1-yl)-2-oxoethyl) amino)benzenesulphonamide (5i)
(N–H of NH2), 3232 (N–H str), 3082 (Ar C–H str), 2853 (aliphatic
C–H str), 1680 (C ¼ O str), 1151 (S ¼ O str), 740 (C–Cl str).
Yield: 68%; Rf: 0.45 (chloroform:methanol 9:1); M.P.: 148–150 ꢀC;
purity (HPLC): 96.06%; 1H-NMR (300 MHz, DMSO-d6)
d ppm:
7.89–7.87 (dd, 2H, Ar–H), 7.54–7.50 (m, 4H, Ar–H), 7.37–7.35 (dd,
1H, Ar–H), 7.05–7.04 (dd, 1H, Ar–H), 6.94–6.92 (dd, 1H, Ar–H), 6.91
(s, 2H, SO2NH2), 6.66–6.64 (dd, 2H, Ar–H), 6.57–6.54 (t, 1H, Ar–NH),
4-((2-(3-(4-Chlorophenyl)-5-(pyridin-4-yl)-4,5-dihydro-1H-pyrazol-1-
yl)-2-oxoethyl)amino) benzenesulphonamide (5e)
Yield: 71%; Rf: 0.41 (chloroform:methanol 9:1); M.P.: 161–164 ꢀC; 5.93–5.89 (dd, 1H, Hx), 4.41–4.28 (dd, 2H, CH2), 3.90–3.83 (dd, 1H,
1H-NMR (300 MHz, DMSO-d6) d ppm: 8.5 (s, 2H, Pyr–H), 7.88–7.85 Ha), 3.41–3.40 (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6):
(dd, 2H, Ar–H), 7.57–7.51 (m, 4H, Ar–H), 7.26–7.24 (dd, 2H, Ar–H), d ¼ 167.3, 154.67, 151.49, 135.8, 131.16, 130.1, 129.31,
6.93 (s, 2H, SO2NH2), 6.68–6.58 (dd, 2H, Ar–H), 6.61–6.58 (t, 1H, 129.03,127.66,127.14, 125.48, 125.2, 111.65, 56.14, 45.13, 41.89; IR
Ar–NH), 5.63–5.57 (dd, 1H, Hx), 4.54–4.32 (dd, 2H, CH2), 3.95–3.85 (ATR, cmꢁ1): 3390, 3308 (N–H of NH2), 3236 (N–H str), 3074 (Ar
(dd, 1H, Ha), 3.25–3.17 (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6): C–H str), 2924 (aliphatic C–H str), 1683 (C ¼ O str), 1157 (S ¼ O str),
d ¼ 168.78, 154.19, 151.09, 149.92, 149.12, 135.22, 130.73, 129.75, 738 (C–Cl str); LC-MS (ESI; M)þ: 475.0.
128.86, 127.18, 120.81, 111.24, 59.23, 44.56, 41.12; IR (ATR, cmꢁ1):
3390, 3309 (N–H of NH2), 3238 (N–H str), 3074 (Ar C–H str), 2926
4-((2-(5-(Anthracen-9-yl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-
(aliphatic C–H str), 1685 (C ¼ O str), 1521 (C ¼ N str), 1153 (S ¼ O
str), 736 (C–Cl str); LC-MS (ESI; M)þ: 469.10.
1-yl)-2-oxoethyl) amino)benzenesulphonamide (5j)
Yield: 71%; Rf: 0.62 (chloroform:methanol 9:1); M.P.: 190–192 ꢀC;
purity (HPLC): 100%; 1H-NMR (300 MHz, DMSO-d6)
d ppm:
4-((2-(3-(4-Chlorophenyl)-5-(2-chlorophenyl)-4,5-dihydro-1H-pyra-
zol-1-yl)-2-oxoethyl) amino)benzenesulphonamide (5f)
8.75–7.61 (m, 4H, Ar–H), 8.22–8.02 (m, 4H, Ar–H), 7.59–7.49 (m,
12H, Ar–H), 6.95–6.92 (dd, 3H, Hx, SO2NH2), 6.75–6.68 (dd, 2H,
Yield: 67%; Rf: 0.47 (chloroform:methanol 9:1); M.P.: 159–162 ꢀC; Ar–H), 6.58–6.55 (t, 1H, Ar–NH), 4.38–4.35 (dd, 2H, CH2), 4.01–4.00
purity (HPLC): 100%; 1H-NMR (300 MHz, DMSO-d6)
d
ppm: (dd, 1H, Ha), 3.35 (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6):
7.88–7.85 (dd, 2H, Ar–H), 7.57–7.51 (m, 5H, Ar–H), 7.29–7.25 (dd, d ¼ 166.86, 151.57, 146.71, 137.28, 134.37, 131.66, 131.38, 131.15,
2H, Ar–H), 7.16 (s, 1H, Ar–H), 6.93 (s, 2H, SO2NH2), 6.69–6.66 (dd, 131.05, 130.07, 129.93, 129.81, 129.4, 128.74, 128.42, 128.21,
2H, Ar–H), 6.63–6.59 (t, 1H, Ar–NH), 5.82–5.77 (dd, 1H, Hx), 127.82, 127.74, 127.52, 125.89, 125.84, 125.55, 125.45, 111.63,
4.57–4.38 (dd, 2H, CH2), 4.02–3.92 (dd, 1H, Ha), 3.29–3.23 (dd, 1H, 44.43, 44.17; IR (ATR, cmꢁ1): 3342 (N–H of NH2), 3277 (N–H str),
Hb); 13C-NMR (100 MHz, DMSO-d6): d ¼ 167.29, 154.58, 151.42, 3051 (Ar C–H str), 2862 (aliphatic C–H str), 1672 (C ¼ O str), 1161
138.82, 135.87, 131.41, 131.24, 130.06, 129.98, 129.4, 129.19, 128.9, (S ¼ O str), 761 (C–Cl str).
127.89, 127.69, 126.9, 111.69, 58.37, 45.15, 41.1; IR (ATR, cmꢁ1):
3267, 3207 (N–H of NH2), 3146 (N–H str), 3097 (Ar C–H str), 2947
4-((2-(3-(4-Chlorophenyl)-5-(1H-indol-3-yl)-4,5-dihydro-1H-pyrazol-
(aliphatic C–H str), 1670 (C ¼ O str), 1195 (S ¼ O str), 759 (C–Cl str);
LC-MS (ESI; M)þ: 503.40.
1-yl)-2-oxoethyl) amino)benzenesulphonamide (5k)
Yield: 73%; Rf: 0.55 (chloroform:methanol 9:1); M.P.: 174–177 ꢀC;
1
purity (HPLC): 100%; H-NMR (300 MHz, DMSO-d6) d ppm: 11.23 (s,
4-((2-(3-(4-Chlorophenyl)-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyra-
zol-1-yl)-2-oxoethyl) amino)benzenesulphonamide (5g)
1H, Indole–NH), 8.23–8.15 (dd, 2H, Ar–H), 7.73–7.71 (dd, 1H, Ar–H),
7.57–7.55 (dd, 2H, Ar–H), 7.44 (dd, 1H, Ar–H), 7.22–7.18 (t, 2H,
Yield: 72%; Rf: 0.41 (chloroform:methanol 9:1); M.P.: 161–163 ꢀC; Ar–H), 6.90 (s, 2H, SO2NH2), 6.71–6.65 (t, 3H, Ar–H, Hx), 6.52–6.49
purity (HPLC): 98.58%; 1H-NMR (300 MHz, DMSO-d6) d ppm: 10.85 (t, 1H, Ar–NH), 4.37–4.31 (dd, 2H, CH2), 3.88–3.86 (dd, 1H, Ha),
(s, 1H, Ar–OH), 7.85–7.78 (m, 3H, Ar–H), 7.55–7.50 (m, 3H, Ar–H), 3.50–3.43 (dd, 1H, Hb); 13C-NMR (100 MHz, DMSO-d6): d ¼ 165.68,
7.48–7.41 (dd, 3H, Ar–H), 6.92 (s, 2H, SO2NH2), 6.69–6.66 (dd, 3H, 151.6, 141.54, 137.53, 131.47, 131.02, 130.3, 127.77, 124.76, 124.58,
Ar–H), 6.48–6.45 (t, 1H, Ar–NH), 4.35–4.32 (dd, 2H, CH2), 4.01–3.99 122.93, 121.94, 120.98, 120.71, 112.26, 111.89, 111.75, 111.56,