POTENTIAL ANTI-INFLAMMATORY AGENTS
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1.01 (t, J ¼ 2.5 Hz, 3H, CH2CH3). Anal. calc. for C12H16N2OS; (236.1): C, 60.99; H,
6.82; N, 11.85. Found: C, 60.88; H, 6.99; N, 11.73.
N-(Benzenesulfonylimino)-4-phenyl-1,2,3,6-tetrahydropyridine (5a). The
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compound 5a was obtained as a white solid; 30% yield, mp 159–160 ꢀC. H NMR
(CDCl3): d 7.97 (d, J ¼ 2.5 Hz, 2H), 7.60 (m, 1H), 7.52 (d, J ¼ 2.5 Hz, 2H),
7.22–7.33 (m, 5H), 5.85 (m, 1H, C5-H), 5.54 (s, 1H, NH, D2O exchangeable), 3.33
(m, 2H, C6-H), 2.87 (t, J ¼ 2.0 Hz, 2H, C2-H), 2.50 (m, 2H, C3-H). Anal. calc. for
C17H18N2O2S (314.40): C, 64.94; H, 5.77; N, 8.91. Found: C, 64.82; H, 5.92; N, 8.87.
N-(2-Furoylamino)-4-phenyl-1,2,3,6-tetrahydropyridine (5b). The com-
pound 5b was obtained as a white solid; 83% yield, mp 193–194 ꢀC. 1H NMR
(CDCl3): d 7.22–7.43 (m, 7H, NH, D2O exchangeable), 7.18 (d, J ¼ 1.0 Hz, 1H,
0
0
C3 -H), 6.49 (dd, J ¼ 0.5, 1.0 Hz, 1H, C4 -H), 6.02 (m, 1H, C5-H), 3.68 (m, 2H, C6-
H), 3.24 (t, J ¼ 2.0 Hz, 2H, C2-H), 2.73 (m, 2H, C3-H). Anal. calc. for
C16H16N2O2 (268.12): C, 71.62; H, 6.01; N, 10.44. Found: C, 71.49; H, 6.12; N, 10.38.
N-(2-Thiophenecarboylamino)-4-phenyl-1,2,3,6-tetrahydropyridine (5c).
The compound 5c was obtained as a white crystalline solid; 73% yield, mp
202–204 ꢀC. 1H NMR (CDCl3): d 8.10 (s, 1H), 7.25–7.55 (m, 6H), 7.08 (t, J ¼ 1.5 Hz,
0
1H), 6.74 (s, 1H, NH, D2O exchangeable), 6.06 (m, 1H, C4 -H), 3.80 (d, J ¼ 5.0 Hz,
1H, C6, H), 3.33 (m, 2H), 2.92–3.10 (m, 2H), 2.60 (d, J ¼ 5.0 Hz, 1H). Anal. calc.
for C16H16N2OS (284.1): C, 67.58; H, 5.67; N, 9.85. Found: C, 67.72; H, 5.71;
N, 9.78.
N-(4-Methylbenzenesulfonylimino)-4-phenyl-1,2,3,6-tetrahydropyridine (5d).
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The compound 5d was obtained as a white solid; 48% yield, mp 164–165 ꢀC. H
NMR (CDCl3): d 7.84 (d, J ¼ 2.7 Hz, 2H), 7.22–7.33 (m, 7H), 5.85 (m, 1H, C5-H),
5.49 (s, 1H, NH, D2O exchangeable), 3.32 (m, 2H, C6-H), 2.87 (t, J ¼ 2.0 Hz, 2H,
0
C2-H), 2.50 (m, 2H, C3-H), 2.42 (s, 3H, C4 -CH3). Anal. calc. for C18H20N2O2S
(328.12): C, 65.83; H, 6.14; N, 8.53. Found: C, 65.96; H, 6.30; N, 8.59.
N-(4-Methylbenzenesulfonylimino)-5-phenyl-1,2,3,6-tetrahydropyridine
(5e). The compound 5e was obtained as a white solid; 25% yield, mp 149–150 ꢀC. 1H
NMR (CDCl3): d 7.85 (d, J ¼ 2.7 Hz, 2H), 7.29 (d, J ¼ 2.7 Hz, 2H), 7.14–7.27 (m,
5H), 6.05 (m, 1H, C4-H), 5.59 (s, 1H, NH, D2O exchangeable), 3.52 (m, 2H, C6-
0
H), 2.78 (t, J ¼ 2.0 Hz, 2H, C2-H), 2.42 (s, 3H, C4 -CH3), 2.28 (m, 2H, C3-H). Anal.
calc. for C18H20N2O2S 0.1 H2O (330.239): C, 65.47; H, 6.10; N, 8.48. Found: C,
65.27; H, 6.29; N, 8.33.
N-(2-Furoylamino)-5-phenyl-1,2,3,6-tetrahydropyridine (5f). The com-
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pound 5f was obtained as a solid; 67% yield, mp 145–146 ꢀC. H NMR (CDCl3): d
7.45 (s, 1H, NH, D2O exchangeable), 7.41 (s, 1H), 7.23–7.32 (m, 5H), 7.17 (d, J ¼ 1.0Hz,
0
0
1H, C3 -H), 6.49 (dd, J ¼ 0.6, 1.2 Hz, 1H, C4 -H), 6.15 (m, 1H, C4-H), 3.87 (m, 2H, C6-
H), 3.16 (t, J ¼ 2.0 Hz, 2H, C2-H), 2.50 (m, 2H, C3-H). Anal. calc. for C16H16N2O2
(268.12): C, 71.62; H, 6.01; N, 10.44. Found: C, 71.51; H, 6.19; N, 10.28.
N-(2-Thiophenecarboylamino)-5-phenyl-1,2,3,6-tetrahydropyridine (5g).
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The compound 5g was obtained as a white solid; 54% yield, mp 154–155 ꢀC. H
NMR (CDCl3): d 8.10 (s, 1H), 7.51 (d, J ¼ 1.6 Hz, 1H), 7.22–7.34 (m, 5H), 7.08 (t,