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(C-8); 163.18 (C-6); 140.42 (C-5); 140.33 (C-10); 135.70
(C-13); 134.60 (C-3); 128.53 (C-12, C-14); 124.16 (C-11,
C-15); 115.55 (C-4); 39.10 (C-16); 36.84 (C-17); 24.09
(C-18); 13.69 (C-19). FT-IR (m, cm-1): 2960; 2348; 1664;
1595; 1530; 1397; 1347; 1306; 1240; 1204; 1147; 1091;
994; 973; 945; 875; 827; 794; 743; 663; 617; 545; 519.
Anal. Calcd for C15H18N4OS: C, 59.58; H, 6.00; N, 18.53;
S, 10.60. Found: C, 59.56; H, 5.99; N, 18.80; S, 10.77.
(bd, 7.5, 1H, H-15); 7.35–7.20 (m, 3H, H-12, H-13, H-14);
3.90 (s, 3H, H-16); 2.9 (sxt, 6.9, 2H, H-17,); 1.55 (q, 6.9,
2H, H-18); 1.16 (d, 6.9, 3H, H-20); 0.75 (t, 6.9, 3H, H-19).
13C-NMR: 181.46 (C-8); 163.65 (C-6); 142.79 (C-10);
140.69 (C-5); 136.30 (C-11); 134.95 (C-3); 128.18 (CH);
127.90 (CH); 126.57 (CH); 126.15 (CH); 115.79 (C-4);
39.16 (C-16); 35.12 (C-17); 30.19 (C-18); 21.22 (C-20);
12.37 (C-19). FT-IR (m, cm-1): 3129; 2956; 1670; 1510;
1319; 1220; 1201; 1149; 1093; 1056; 995; 878; 830; 758;
712; 688; 655; 610; 537; 461. Anal. Calcd for
C16H20N4OS: C, 60.73; H, 6.37; N, 17.71; S, 10.13. Found:
C, 60.44; H, 6.76; N, 17.46; S, 9.86.
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(2-i-proylphenyl)-thiourea (4h)
Prepared using the general procedure. Yield 65%, m.p.
1
177.5–179°C (isopropanol). H-NMR: 12.41 (s, NH, H-9);
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(4-s-butylphenyl)-thiourea (4k)
11.40 (s, NH, H-7); 8.60 (s, 1H, H-3); 8.22 (s, 1H, H-5);
7.41 (dd, 7.5, 1.8, 1H, H-12); 7.38 (dd, 7.5, 1.8, 1H, H-15);
7.30 (td, 7.5, 1.8, 1H, H-13); 7.23 (td, 7.5, 1.8, 1H, H-14);
3.89 (s, 3H, H-16); 3.04 (septet, 6.7, 1H, H-17); 1.18 (d,
6.7, 6H, H-18). 13C-NMR: 181.26 (C-8); 163.33 (C-6);
143.74 (C-10); 140.46 (C-5); 135.64 (C-11); 134.69 (C-3);
127.96 (C-12); 127.71 (C-13); 125.98 (C-14); 125.86
(C-15); 115.58 (C-4); 39.12 (C-16); 27.99 (C-17); 23.07
(C-18). FT-IR (m, cm-1): 3181; 2968; 1670; 1552; 1508;
1398; 1363; 1315; 1243; 1217; 1200; 1156; 1097; 1063;
1028; 995; 977; 937; 866; 834; 780; 762; 720; 689; 664;
643; 620; 582; 557; 532; 469; 439; 419. Anal. Calcd for
C15H18N4OS: C, 59.58; H, 6.00; N, 18.53; S, 10.60. Found:
C, 59.44; H, 6.07; N, 18.68; S, 10.76.
Prepared using the general procedure. Yield 70%, m.p.
1
151–152°C (isopropanol). H-NMR: 12.4 (bs, NH, H-9);
11.4 (s, NH, H-7); 8.53 (s, 1H, H-3); 8.15 (s, 1H, H-5); 7.58
(d, 8.5, 2H, H-12, H-14), 7.21 (d, 8.5, 2H, H-11, H-15),
3.90 (s, 3H, H-16); 2.60 (sxt, 7.1, 2H, H-17,); 1.55 (q, 7.1,
2H, H-18); 1.19 (d, 6.9, 3H, H-20); 0.77 (t, 7.1, 3H, H-19).
13C-NMR: 183.61 (C-8); 163.64 (C-6); 144.74 (C-10);
140.32 (C-5); 136.07 (C-11); 134.38 (C-3); 126.24 (CH);
126.07 (CH); 110.28 (C-4); 38.96 (C-16); 31.26 (C-18);
30.53 (C-17); 21.71 (C-20); 12.11 (C-19). FT-IR (m, cm-1):
2986; 2901; 1661; 1587; 1516; 1452; 1393; 1315; 1251;
1201; 1147; 1066; 877; 825; 757; 672; 613; 547. Anal.
Calcd for C16H20N4OS: C, 60.73; H, 6.37; N, 17.71; S,
10.13. Found: C, 60.46; H, 6.71; N, 17.55; S, 9.81.
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(4-i-proylphenyl)-thiourea (4i)
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(2-t-butylphenyl)-thiourea (4l)
Prepared using the general procedure. Yield 69%, m.p.
1
127–128°C (isopropanol). H-NMR: 12.10 (bs, NH, H-9);
11.29 (s, NH, H-7); 8.59 (s, 1H, H-3); 8.21 (s, 1H, H-5); 7.55
(d, 8.4, 2H, H-11, H-15); 7.26 (d, 8.4, 2H, H-12, H-14); 3.89
(s, 3H, H-16); 2.89 (septet, 6.9, 1H, H-17); 1.19 (d, 6.9, 6H,
H-18). 13C-NMR: 179.47 (C-8); 163.39 (C-6); 146.76
(C-13); 140.65 (C-5); 135.95 (C-10); 134.84 (C-3); 126.74
(C-12, C-14); 124.54 (C-11, C-15); 115.84 (C-4); 39.34
(C-16); 33.33 (C-17); 24.12 (C-18). FT-IR (m, cm-1): 3286;
3110; 3034; 2952; 1662; 1596; 1530; 1511; 1398; 1343;
1295; 1246; 1206; 1146; 1090; 1063; 1016; 994; 945; 918;
873; 830; 811; 761; 728; 664; 617; 548; 523; 480; 433. Anal.
Calcd for C15H18N4OS: C, 59.58; H, 6.00; N, 18.53; S,
10.60. Found: C, 59.87; H, 5.80; N, 18.70; S, 10.71.
Prepared using the general procedure. Yield 66%, m.p.
1
146–147.5°C (isopropanol). H-NMR: 12.30 (s, NH, H-9);
11.46 (s, NH, H-7); 8.62 (s, 1H, H-3); 8.24 (s, 1H, H-5); 7.44
(dd, 7.0, 2.6, 1H, H-15); 7.25–7.35 (m, 3H, H-12, H-13, H-
14); 3.89 (s, 3H, H-16); 1.33 (s, 9H, H-18). 13C-NMR: 181.29
(C-8); 163.59 (C-6); 145.03 (C-10); 140.50 (C-5); 136.32 (C-
11); 134.82 (C-3); 131.18 (C-14); 127.57 (CH); 126.73 (CH);
126.38 (CH); 115.48 (C-4); 39.12 (C-16); 34.57 (C-17); 30.50
(C-18). FT-IR (m, cm-1): 3125; 2972; 2901; 1657; 1517;
1443; 1396; 1315; 1232; 1214; 1200; 1149; 1066; 990; 935;
877; 846; 825; 763; 745; 683; 616; 547; 485; 438. Anal. Calcd
for C16H20N4OS: C, 60.73; H, 6.37; N, 17.71; S, 10.13.
Found: C, 60.90; H, 6.33; N, 17.74; S, 10.35.
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(2-s-butylphenyl)-thiourea (4j)
N-[(1-methyl-1H-pyrazole-4-yl)carbonyl]-N0-
(4-t-butylphenyl)-thiourea (4m)
Prepared using the general procedure. Yield 66%, m.p.
1
153–154°C (isopropanol). H-NMR: 12.4 (bs, NH, H-9);
11.4 (s, NH, H-7); 8.60 (s, 1H, H-3); 8.22 (s, 1H, H-5); 7.42
Prepared using the general procedure. Yield 70%, m.p.
1
152–153°C (isopropanol). H-NMR: 12.74 (s, NH, H-9);
123