S. Subramanian et al. / European Journal of Medicinal Chemistry 46 (2011) 3258e3264
3263
140.2, 129.6, 128.9, 128.4, 127.4, 125.9, 125.7, 116.3, 52.5, 41.5, 40.3,
39.5, 26.3, 20.1; HRMS calcd for C18H19N3O3S m/z 357.1147, found
357.1138.
6.3.7. Allyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihyd-
roquinoline-1(2H)-carboxylate (4g)
Yield 40.8%; White solid; mp 139.8e141.2 ꢁC; IR (KBr) 3400,
3050, 2930, 1740, 1700, cmꢀ1 1H NMR (DMSO-d6)
1.89 (quin,
;
d
6.3.2. Methyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihyd-
roquinoline-1(2H)-carboxylate (4b)
J ¼ 5.6 Hz, 2H), 2.81 (t, J ¼ 6.5 Hz, 2H), 3.51 (dd, J ¼ 7.3, 9.8 Hz, 1H),
3.78 (t, J ¼ 6.4 Hz, 2H), 4.29 (t, J ¼ 9.2 Hz, 1H), 4.65e4.74 (m, 2H),
4.80 (dd, J ¼ 7.2, 9.5 Hz, 1H), 5.18e5.47 (m, 2H), 5.81e6.24 (dd,
11.3, 5.7, H), 7.18e8.01 (m, 8H), 8.20 (bs, exchangeable with D2O,
Yield 41.8%; White solid; mp 209.0e209.5 ꢁC; IR (KBr) 3210,
3100, 2930, 1720 cmꢀ1
; d 1.88 (quin,
1H NMR (DMSO-d6)
J ¼ 6.0 Hz, 2H), 2.81(t, J ¼ 5.9 Hz, 2H), 3.52 (dd, J ¼ 7.3, 9.2 Hz, 1H),
3.68 (dd, J ¼ 7.3, 9.8 Hz, 2H), 3.76 (s, 3H), 4.27 (dd, J ¼ 9.6 Hz, 1H),
4.81 (dd, J ¼ 7.2, 9.3 Hz, 1H), 7.19e8.01 (m, 8H), 8.22 (bs,
1H); 13C NMR (DMSO-d6)
d
¼ 154.9, 154.0, 143.1, 139.0, 131.9, 131.2,
130.0, 128.9, 128.6, 125.7, 125.5, 123.3, 118.2, 66.6, 52.6, 52.3, 44.9,
27.2, 22.3; HRMS calcd for C22H23N3O5S m/z 441.1358, found
441.1356.
exchangeable with D2O, 1H); 13C NMR (DMSO-d6)
143.4, 139.6, 132.1, 130.8, 129.6, 129.3, 126.4, 125.9, 124.1, 66.1,
53.3, 52.7, 45.7, 27.9, 22.9; HRMS calcd for C20H21N3O5S m/z
415.1202, found 415.1206.
d
¼ 155.1, 154.3,
6.3.8. 2-Chloroethyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,
4-dihydroquinoline-1(2H)-carboxylate (4h)
Yield 28.3%; White solid; mp 178.3e179.4 ꢁC; IR (KBr) 3210,
6.3.3. Ethyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihyd-
roquinoline-1(2H)-carboxylate (4c)
3100, 2950, 1720 cmꢀ1; 1H NMR (DMSO-d6)
d
1.90 (quin, J ¼ 6.1 Hz,
2H), 2.82 (t, J ¼ 6.1 Hz, 2H), 3.63 (dd, J ¼ 7.2, 9.8 Hz, 1H), 3.78 (t,
J ¼ 6.2 Hz, 2H), 3.93 (t, J ¼ 4.8 Hz, 2H), 4.29 (dd, J ¼ 8.3, 8.9 Hz, 2H),
4.43 (t, J ¼ 4.8 Hz, 1H), 4.81 (dd, J ¼ 7.0, 9.3 Hz, 1H), 7.27e7.92 (m,
8H), 8.22 (bs, exchangeable with D2O, 1H); 13C NMR (DMSO-d6)
Yield 79.3%; White solid; mp 213.9e214.6 ꢁC; IR (KBr) 3210,
3100, 2920, 1720 cmꢀ1; 1H NMR (DMSO-d6)
d
1.27 (t, J ¼ 7.0 Hz, 3H),
1.88 (quin, J ¼ 5.9 Hz, 2H), 2.81(t, J ¼ 5.9 Hz, 2H), 3.52 (dd, J ¼ 7.2,
9.8 Hz, 1H), 3.75 (t, J ¼ 5.9 Hz, 2H), 4.21(q, J ¼ 7.0 Hz, 2H), 4.29 (t,
J ¼ 9.5 Hz, 1H), 4.81 (dd, J ¼ 7.2, 9.4 Hz, 1H), 7.19e8.02 (m, 8H), 8.22
d
¼ 154.9, 153.7, 142.8, 139.0, 131.5, 130.2, 128.9, 128.6, 126.4, 125.7,
123.5, 65.5, 53.4, 52.7, 45.0, 41.6, 27.3, 22.3; HRMS calcd for
(bs, exchangeable with D2O, 1H); 13C NMR (DMSO-d6)
d
¼ 155.4,
C21H22ClN3O5S m/z 463.0969, found 463.0962.
154.8, 143.7, 139.5, 131.4, 130.4, 129.3, 129.0, 129.0, 126.1, 125.9,
123.7, 62.5, 53.0, 52.8, 45.2, 27.7, 22.7, 14.5; HRMS calcd for
C21H23N3O5S m/z 429.1358, found 429.1350.
6.3.9. 1-(1-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-6-ylsulfonyl)-
4-phenylimidazolidin-2-one (4i)
Yield 14.8%; White solid; mp 207.8e208.8 ꢁC; IR (KBr) 3100,
6.3.4. Propyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihyd-
roquinoline-1(2H)-carboxylate (4d)
2950, 2350, 1720 cmꢀ1; 1H NMR (DMSO-d6)
2H), 2.90 (t, J ¼ 6.2 Hz, 2H), 3.59 (dd, J ¼ 7.0, 9.5 Hz, 1H), 3.82 (t,
J ¼ 6.2 Hz, 1H), 4.29 (t, J ¼ 9.6 Hz, 1H), 4.81 (dd, J ¼ 7.3, 9.5 Hz, 1H),
7.13e7.98 (m, 8H), 8.06 (bs, exchangeable with D2O, 1H); 13C NMR
d
2.04 (quin, J ¼ 6.2 Hz,
Yield 63.4%; White solid; mp 213.9e214.8 ꢁC; IR (KBr) 3320,
3100, 2940,1720 cmꢀ1; 1H NMR (DMSO-d6)
d
0.94 (t, J ¼ 6.8 Hz, 3H),
1.64 (m, 2H), 1.89(quin, J ¼ 6.8 Hz, 2H), 2.82 (t, J ¼ 6.6 Hz, 2H), 3.52
(dd, J ¼ 7.2, 9.5 Hz,1H), 3.77 (t, J ¼ 6.6 Hz, 2H), 4.13 (t, J ¼ 6.2 Hz, 2H),
4.30 (t, J ¼ 9.6 Hz, 1H), 4.81 (dd, J ¼ 7.3, 9.4 Hz, 1H), 7.20e8.02 (m,
8H), 8.21(bs, exchangeable with D2O, 1H); 13C NMR (DMSO-d6)
(DMSO-d6)
d
¼ 166.7, 155.9, 143.9, 138.8, 133.2, 129.6, 129.4, 128.8,
126.6, 126.0, 125.0, 52.6, 52.2, 45.5, 44.3, 25.8, 23.3; HRMS calcd for
C20H20ClN3O4S m/z 433.0863, found 433.0856.
d
¼ 155.4, 154.8, 143.3, 139.4, 132.2, 129.6, 129.3, 126.9, 126.1, 125.4,
6.3.10. 1-(1-Benzoyl-1,2,3,4-tetrahydroquinolin-6-ylsulfonyl)-4-phe-
nylimidazolidin-2-one (4j)
124.1, 68.8, 53.7, 52.6, 45.4, 27.1, 22.1, 21.6, 9.9; HRMS calcd for
C22H25N3O5S m/z 443.1515, found 443.1502.
Yield 96.0%; White solid; mp 213.1e214.5 ꢁC; IR (KBr) 3270,
2910, 1720, 1620 cmꢀ1; 1H NMR (DMSO-d6)
2H), 2.92 (t, J ¼ 6.8 Hz, 2H), 3.49 (m, 1H), 3.78 (t, J ¼ 6.4 Hz, 2H), 4.27
(t, J ¼ 9.2 Hz, 1H), 4.80 (dd, J ¼ 7.2, 8.9 Hz, 1H), 7.15e7.77 (m, 13H),
8.22 (bs, exchangeable with D2O, 1H); 13C NMR (DMSO-d6)
d
1.96 (quin, J ¼ 6.2 Hz,
6.3.5. Isobutyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihy-
droquinoline-1(2H)-carboxylate (4e)
Yield 62.6%; White solid; mp 190.0e191.0 ꢁC; IR (KBr) 3220,
3100, 2950, 1720, 1700, cmꢀ1
;
1H NMR (DMSO-d6)
d
0.94 (d,
d
¼ 171.0, 155.5, 144.2, 139.4, 135.3, 133.9, 131.1, 130.9, 129.0, 128.9,
J ¼ 6.6 Hz, 6H), 1.89 (quin, J ¼ 6.4 Hz, 2H), 2.81(t, J ¼ 6.4 Hz, 2H),
3.51 (dd, J ¼ 7.2, 9.2 Hz, 1H), 3.78 (t, J ¼ 6.4 Hz, 2H), 3.96 (d,
J ¼ 6.6 Hz, 2H), 4.30 (t, J ¼ 9.6 Hz, 1H), 4.81 (dd, J ¼ 7.2, 9.2 Hz,
1H), 7.34e8.01 (m, 8H), 8.22 (bs, exchangeable with D2O, 1H);
128.4, 128.3, 125.8, 125.2, 125.1, 52.7, 52.5, 45.4, 26.9, 23.1; HRMS
calcd for C25H23N3O4S m/z 461.1409, found 461.1398.
6.3.11. 4-Phenyl-1-(1-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroquino-
lin-6-ylsulfonyl)imidazolidin-2-one (4k)
13C NMR (DMSO-d6)
d
¼ 155.9, 154.9, 143.6, 139.9, 131.5, 130.4,
129.3, 128.9, 126.2, 126.0, 123.7, 72.7, 53.0, 52.8, 45.3, 28.0, 27.8,
22.8, 19.3; HRMS calcd for C23H27N3O5S m/z 457.1671, found
457.1666.
Yield 74.8%; White solid; mp 166.7e171.1 ꢁC; IR (KBr) 3210, 3110,
2910, 1730, 1690 cmꢀ1; 1H NMR (DMSO-d6)
d
2.03 (quin, J ¼ 6.2 Hz,
2H), 2.93 (t, J ¼ 6.2 Hz, 2H), 3.55 (dd, J ¼ 7.2, 9.3 Hz, 1H), 3.88 (t,
J ¼ 6.3 Hz, 2H), 4.33 (t, J ¼ 9.4 Hz, 1H), 4.83 (dd, J ¼ 7.2, 9.5 Hz, 1H),
7.17e7.46 (m, 5H), 7.83 (s, 3H), 8.27 (bs, exchangeable with D2O,
6.3.6. Butyl 6-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihyd-
roquinoline-1(2H)-carboxylate (4f)
1H); 13C (DMSO-d6)
128.9, 125.9, 125.6, 125.1, 117.8, 114.94, 52.9, 52.6, 45.0, 26.0, 22.8;
d
¼ 155.9, 155.2, 141.7, 139.3, 134.9, 129.5, 129.2,
Yield 49.2%; White solid; mp 145.5e146.0 ꢁC; IR (KBr) 3220,
3100, 2950, 1720, 1700, cmꢀ1
;
1H NMR (DMSO-d6)
d
0.90 (t,
HRMS calcd for C20H18F3N3O4S m/z 453.0970, found 453.0962.
J ¼ 6.2 Hz, 3H), 1.16e1.71 (m, 4H), 1.86 (quin, J ¼ 5.7 Hz, 2H), 2.79 (t,
J ¼ 6.1 Hz, 2H), 3.50 (dd, J ¼ 7.2, 9.5 1H), 3.74 (t, J ¼ 6.2 Hz, 2H), 4.16
(t, J ¼ 6.4 Hz, 2H), 4.27 (t, J ¼ 9.4 Hz, 1H), 4.78 (dd, J ¼ 7.2, 9.3 Hz,
1H), 7.17e7.99 (m, 8H), 8.20 (bs, exchangeable with D2O, 1H); 13C
6.3.12. 6-(2-Oxo-4-phenylimidazolidin-1-ylsulfonyl)-3,4-dihydro-
quinoline-1(2H)-carboxamide (4l)
Yield 70%; White solid; mp 168.8e170.4 ꢁC; IR (KBr) 3350, 3200,
NMR (DMSO-d6)
d
¼ 155.3, 154.2, 142.7, 139.4, 132.5, 131.0, 129.6,
3100, 2900, 1750, 1650 cmꢀ1 1H NMR (DMSO-d6)
; d 1.87 (quin,
129.2, 126.9, 126.1, 125.8, 125.1, 67.0, 56.2, 55.4, 45.2, 30.2, 27.0, 23.1,
18.5, 13.4; HRMS calcd for C23H27N3O5S m/z 457.1671, found
457.1662.
J ¼ 5.9 Hz, 2H), 2.75 (t, J ¼ 6.2 Hz, 2H), 3.43 (bs, exchangeable with
D2O, 2H), 3.63 (t, J ¼ 5.9 Hz, 2H), 4.26 (t, J ¼ 9.5 Hz, 1H), 4.80 (dd,
J ¼ 7.2, 9.4 Hz, 1H), 6.68 (bs, exchangeable with D2O, 1H), 7.28e7.81