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K. Srikanth et al. / Bioorg. Med. Chem. 10 (2002) 1841–1854
1,5-N,N 0-di i-Propyl-2-(benzenesulphonyl) glutamamide
CH2-2000, CH2-3000 CH2-4000, CH2-5000), 1.08 (m, 6H, CH3-
600, CH3-6000). IR (KBr, cmÀ1): 3299, 3232, 3170 (N–H
str of CONH), 3021 (Ar–C–H str), 2897, 2877 (ali C–H
str), 1643 (C¼O str), 1625, 1543, 1444 (ali C–H def),
1328, 1313 and 1157 (S¼O str of SO2NH), 1084, 970,
710, 672 (Ar–C–H def). Anal. C23H39N3O4S1 (C, H, N)
calcd: 59.10, 8.35, 8.99; found: 59.09, 8.07, 8.84.
1
(7). MS (FAB): M+H+ peak at m/z 370. H NMR
(200 MHz, CDCl3): d 7.91 (m, 2H, H-20, H-60), 7.36–
7.25 (m, 2H, H-30, H-40, H-50), 7.09 (s, 1H, SO2NH),
6.40 (m, 1H, CONH), 5.79 (m, 1H, CONH), 3.96 (m,
1H, CH-1000), 3.87 (m, 1H, CH-100), 3.48 (m, 1H, H-2),
2.31 (m, 1H, HA-3), 2.12 (m, 1H, HB-3), 1.97 (m, 2H,
H2-4,), 1.35–1.21 (m, 6H, CH3-2000, CH3-3000), 0.97–0.89
(m, 6H, CH3-200, CH3-300). IR (KBr, cmÀ1): 3241, 3178
(N–H str of CONH), 3001 (Ar–C–H str), 2878 (ali C–H
str), 1624, 1529, 1437 (ali C–H def), 1328 and 1152
(S¼O str of SO2NH), 1084, 773, 748 and 714 (Ar–C–H
def), 675. Anal. C17H27N3O4S1 (C, H, N) calcd: 55.28,
7.32, 11.38; found: 55.18, 7.28, 11.70.
1,5-N,N 0-di-Cyclohexyl-2-(40-methyl benzenesulphonyl)
glutamamide (12). MS (FAB): M+H+ peak at m/z
450. H NMR (500 MHz, CDCl3): d 7.71 (m, 2H, H-20,
1
H-60), 7.28 (d, 2H, H-30, H-50), 7.01 (s, 1H, SO2NH),
6.62 (d, 1H, CONH), 6.46 (d, 1H, CONH), 3.76 (m, 1H,
H-2), 3.68 (m, 1H, CH-1000), 3.62–3.46 (m, 1H, CH-100),
2.40 (s, 3H, Ar–CH3), 2.35–2.20 (m, 2H, H2-3), 2.13–
2.07 (m, 2H, H2-4), 1.92–1.00 (m, 20H, cyclohexyl pro-
tons). IR (KBr, cmÀ1): 3240, 3187 (N–H str of CONH),
2876, 2804(ali C–H str), 1626 (C ¼O str), 1531, 1436 (ali
C–H def), 1326 and 1155 (S¼O str of SO2NH), 1083,
664(Ar–C–H def). Anal. C 23H35N3O4S1 (C, H, N)
calcd: 61.47, 7.79, 9.35; found: 61.54, 8.11, 9.13.
1,5-N,N 0-di-(Dimethyl)-2-(benzenesulphonyl) glutama-
mide (8). MS (FAB): M+H+ peak at m/z 314. 1H
NMR (200 MHz, CDCl3): d 7.97 (m, 2H, H-20, H-60),
7.42–7.29 (m, 3H, H-30, H-40, H-50), 7.11 (s, 1H,
SO2NH), 3.11 (m, 6H, CH3-1000, CH3-2000), 2.95 (m, 6H,
CH3-100, CH3-200), 2.60 (m, 1H, H-2), 2.31 (m, 2H, H2-
4), 1.86 (m, 1H, HA-3), 1.54(m, 1H, H B-3). IR (KBr,
cmÀ1): 3371, 3032 (Ar–C–H str), 2875 (ali C–H str),
1632 (C¼O str overlapped with N–H bend), 1480, 1342
and 1158 (S¼O str of SO2NH), 1117, 757 and 702 (Ar–
C–H def), 662. Anal. C13H19N3O4S1 (C, H, N) calcd:
49.84, 6.07, 13.41; found: 49.75, 6.21, 13.42.
1,5-N,N 0-di i-Propyl-2-(40-methyl benzenesulphonyl) glu-
tamamide (13). MS (FAB): M+H+ peak at m/z 370.
1H NMR (500 MHz, CDCl3): d 7.71 (d, 2H, J=8.20, H-
20, H-60), 7.26 (d, 2H, J=7.97, H-30, H-50), 7.05 (s, 1H,
SO2NH), 6.56 (d, 1H, CONH), 5.59 (d, 1H, CONH),
4.06 (m, 1H, CH-100), 3.87 (m, 1H, CH-1000), 3.57 (m, 1H,
H-2), 2.40 (s, 3H, Ar–CH3), 2.32 (m, 1H, HA-3), 2.08
(m, 1H, HB-3), 1.89–1.85 (m, 2H, H2-4), 1.19–1.16 (m,
6H, CH3-2000, CH3-3000), 1.07 (m, 3H,CH3-200), 0.97 (m,
3H, CH3-300).IR (KBr, cmÀ1): 3238, 3176 (N–H str of
CONH), 2912 and 2876 (ali C–H str), 1623, 1531,
1433 (ali C–H def), 1328 and 1152 (S¼O str of
SO2NH), 1083, 671 (Ar–C–H def). Anal. C17H27N3O4S1
(C, H, N) calcd: 55.28, 7.32, 11.38; found: 55.27, 7.52,
11.57.
1,5-N,N 0-di-(Diethyl)-2-(benzenesulphonyl) glutamamide
1
(9). MS (FAB): M+H+ peak at m/z 398. H NMR
(200 MHz, CDCl3): d 8.05 (m, 2H, H-20, H-60), 7.62–
7.46 (m, 3H, H-30, H-40, H-50), 7.10 (m, 1H, SO2NH),
3.52 (m, 1H, H-2), 3.48–3.32 (m, 8H, N–CH2-1000, N-
CH2-3000, N–CH2-100, N–CH2-300), 2.66 (m, 2H, H2-4),
2.42 (m, 1H, HA-3), 2.36 (m, 1H, HB-3), 1.31 (m, 6H,
CH3-2000, CH3-4000), 1.15 (m, 6H, CH3-200, CH3-400). IR
(KBr, cmÀ1): 3035 (Ar–C–H str), 2881 (ali C–H str),
1634(C ¼O str), 1440 (ali C–H def), 1345 and 1164
(S¼O str of SO2NH), 1114, 765 and 722 (Ar–C–H def),
684. Anal. C19H31N3O4S1 (C, H, N) calcd: 57.43, 7.81,
10.58; found: 57.34, 7.91, 10.30.
1,5-N,N 0-di i-Butyl-2-(40-methyl benzenesulphonyl) glu-
tamamide (14). MS (FAB): M+H+ peak at m/z 412.
1H NMR (200 MHz, CDCl3): d 7.71 (m, 2H, H-20, H-
60), 7.28–7.17 (m, 3H, H-30, H-50, SO2NH), 6.87 (m, 1H,
CONH), 5.75 (m, 1H, CONH), 3.61 (m, 1H, H-2), 3.08
(m, 2H, N–CH2-1000), 2.96 (m, 2H, N–CH2-100), 2.40 (s,
3H, Ar–CH3), 1.93–1.62 (m, 4H, H2-3, H2-4), 1.32–1.20
(m, 2H, CH-200, CH-2000), 0.94–0.80 (m, 12H, CH3-300,
CH3-400, CH3-3000, CH3-4000). IR (KBr, cmÀ1): 3299, 3240,
3167 (N–H str of CONH), 3032 (Ar–C–H str), 2900,
2876 (ali C–H str), 1648, 1628, 1538, 1443, 1424 (ali C–
H def), 1334and 1312, 1158 (S ¼O str of SO2NH), 1084,
972, 745, 699 (Ar–C–H def), 671. Anal. C20H33N3O4S1
(C, H, N) calcd: 55.20, 7.51, 10.17; found: 55.17, 7.49,
10.18.
1,5-N,N 0-di-Benzyl-2-(40-methyl benzenesulphonyl) glu-
tamamide (10). MS (FAB): M+H+ peak at m/z 480.
1H NMR (200 MHz, CDCl3): d 7.65 (d, 2H, H-20, H-60),
7.48–7.19 (m, 13H, H-30, H-50, SO2NH, ph-protons),
6.83 (m, 2H, CONH-1, CONH-5), 4.38 (m, 2H, CH2-
ph), 4.35 (m, 2H, CH2-ph), 3.79 (m, 1H, H-2), 2.39 (s,
3H, Ar–CH3), 2.35 (m, 2H, H2-4), 2.09–1.94 (m, 2H,
H2-3). IR (KBr, cmÀ1): 3295, 3196 (N–H str of CONH),
2975, 2874, 1700 (C¼O str of CONH), 1554, 1441, 1324
and 1154(S ¼O str of SO2NH), 981, 791, 719 (Ar–C–H
def), 691, 677. Anal. C25H27N3O4S1 (C, H, N) calcd:
62.63, 5.63, 8.76; found: 62.43, 5.43, 8.54.
1,5-N,N 0-di-(Diisopropyl)-2-(40-methyl benzenesulphonyl)
glutamamide (15). MS (FAB): M+H+ peak at m/z 454.
1H NMR (500 MHz, CDCl3): d 7.73 (d, 2H, J=8.20, H-
20, H-60), 7.28 (d, 2H, J=8.18, H-30, H-50), 7.00 (s, 1H,
SO2NH), 4.06 (m, 2H, CH-100, CH-400), 3.87–3.79 (m,
2H, CH-1000, CH-4000), 3.56 (m, 1H, H-2), 2.40 (s, 3H,
Ar–CH3), 2.33 (m, 1H, HA-3), 2.09 (m, 1H, HB-3), 1.90–
1.85 (m, 2H, H2-4), 1.23–1.14 (m, 12H, CH3-2000, CH3-
3000, CH3-5000, CH3-6000), 1.06–0.84(m, 12H, CH 3-200,
1,5-N,N 0-di n-Hexyl-2-(40-methyl benzenesulphonyl) glu-
tamamide (11). MS (FAB): M+H+ peak at m/z 468.
1H NMR (200 MHz, DMSO): d 8.30 (m, 1H, SO2NH),
8.00 (m, 2H, H-20, H-60), 7.87 (m, 2H, H-30, H-50), 7.57
(m, 2H, CONH-1, CONH-5), 3.98 (m, 1H, H-2), 3.21
(m, 2H, N–CH2-1000), 3.03 (m, 2H, N–CH2-100), 2.59 (s,
3H, Ar–CH3), 2.27 (m, 2H, H2-4), 1.88 (m, 2H, H2-3),
1.57–1.39 (m, 16H, CH2-200, CH2-300, CH2-400, CH2-500,