Med Chem Res (2013) 22:3160–3169
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1-(5-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)-3-methoxyphenyl)-4,5-dihydro-3-(4-
methoxyphenyl)pyrazol-1-yl)ethanone (JGPT-4)
60.38; H, 5.23; N, 13.63. Found: C, 60.03; H, 5.64; N,
13.37. HRMS m/z: 639.1101 (M??Na)
1-(3-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)phenyl)-4,5-dihydro-5-(4-
methoxyphenyl)pyrazol-1-yl)ethanone (JGPT-7)
% Yield: 73 %; mp: 91–93 °C; I.R. (KBr, cm-1): 1660
(C=O, stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1270 (C–O, stretch), 1130 (C–N,
% Yield: 71 %, semisolid; I.R. (KBr, cm-1): 1660 (C=O,
stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1130 (C–N, stretch); 1H NMR (CDCl3,
400 MHz, d, TMS = 0): 8.24 (2H, d, J = 8.0 Hz), 7.68
(2H, d, J = 8.4 Hz), 7.63 (1H,s), 7.41 (2H, d, J = 8.0 Hz),
7.15 (2H, d, J = 8.4 Hz), 7.01 (2H, d, J = 8.4 Hz), 6.83
(2H, d, J = 8.0 Hz), 5.63 (2H, s), 5.53 (1H, dd, J = 4 and
11.6 Hz), 5.26 (2H, s), 3.76 (3H, s), 3.68 (1H, dd, J = 11.6
and 17.2 Hz), 3.11 (1H, dd, J = 4 and 17.2 Hz), 2.30 (3H,
s); Anal. Calcd for C28H26N6O5: C, 63.87; H, 4.98; N,
15.96. Found: C, 64.19; H, 4.75; N, 16.27. HRMS m/z:
549.1830 (M??Na).
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stretch); H NMR (CDCl3, 300 MHz, d, TMS = 0): 8.24
(2H, d, J = 9.3 Hz), 7.68 (2H, d, J = 8.7 Hz), 7.6 (1H, s),
7.38 (2H, d, J = 8.4 Hz), 6.90–6.9 (3H, m), 6.70–6.75 (2H,
m), 5.61 (2H, s), 5.49 (1H, dd, J = 4.2 and 11.4 Hz), 5.25
(2H, s), 3.85 (3H, s), 3.80 (3H, s), 3.70 (1H, dd, J = 11.4
and 17.7 Hz), 3.10 (1H, dd, J = 4.2 and 17.7 Hz), 2.40
(3H, s); 13C NMR (CDCl3, 75.4 MHz): 168.12, 158.73,
147.13, 145.91, 139.19, 139.23, 129.67, 128.87, 126. 93.
124. 66, 122.14, 113.62, 65.31, 59.51, 55.31, 50.19, 29.16
Anal. Calcd for C29H28N6O6: C, 62.58; H, 5.07; N, 15.10.
Found: C, 62.47; H, 5.39; N, 14.88. HRMS m/z: 579.1957
(M??Na)
1-(5-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)-3-methoxyphenyl)-4,5-dihydro-3-(4-
nitrophenyl)pyrazol-1-yl)ethanone (JGPT-5)
1-(3-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)phenyl)-4,5-dihydro-5-(3,4-
dimethoxyphenyl)pyrazol-1-yl)ethanone (JGPT-8)
% Yield: 68 %; mp: 65–68 °C; I.R. (KBr, cm-1): 1660
(C=O, stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1130 (C–N, stretch); 1H NMR (CDCl3,
300 MHz, d, TMS = 0): 8.27 (2H, d, J = 8.7 Hz), 8.22
(2H, d, J = 8.1 Hz), 7.88 (1H, d, J = 8.4 Hz), 7.60 (1H,
s), 7.49 (1H, d, J = 8.4 Hz), 7.38 (2H, d, J = 8.7 Hz), 6.96
(1H, d, J = 8.1 Hz), 6.69–6.75 (2H, m), 5.61 (2H, s), 5.60
(1H, dd, J = 4.2 and 11.4 Hz), 5.25 (2H, s), 3.81 (3H, s),
3.70 (1H, dd, J = 11.4 and 17.7 Hz), 3.18 (1H, dd, J = 4.2
and 17.7 Hz), 2.40 (3H, s); Anal. Calcd for C28H25N7O7:
C, 58.84; H, 4.41; N, 17.15. Found: C, 59.23; H, 4.08; N,
17.49. HRMS m/z: 594.1010 (M??Na).
% Yield: 67 %; semisolid; I.R. (KBr, cm-1): 1660 (C=O,
stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1270 (C–O, stretch), 1130 (C–N,
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stretch); H NMR (CDCl3, 300 MHz, d, TMS = 0): 8.23
(2H, d, J = 7.2 Hz), 7.70 (2H, d, J = 8.7 Hz), 7.61 (1H,
s), 7.53 (2H, d, J = 8.7 Hz), 7.08 (2H, d, J = 9.0 Hz),
6.65–6.85 (3H, m), 5.78 (2H, S), 5.46 (1H, dd, J = 4.2 and
11.4 Hz), 5.21 (2H, s), 3.77 (6H, s), 3.70 (1H, dd, J = 11.4
and 17.7 Hz), 3.10 (1H, dd, J = 4.2 and 17.7 Hz), 2.52
(3H, s); Anal. Calcd for C29H28N6O6: C, 62.58; H, 5.07; N,
15.10 Found: C, 62.32; H, 5.44; N, 14.75. HRMS m/z:
579.1231 (M??Na).
1-(5-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)-3-methoxyphenyl)-4,5-dihydro-3-(3,4,5-
trimethoxyphenyl)pyrazol-1-yl)ethanone (JGPT-6)
1-(5-(4-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-
yl)methoxy)-3-methoxyphenyl)-4,5-dihydro-3-
phenylpyrazol-1-yl)ethanone (JGPT-9)
% Yield: 63 %, mp: 88–90 °C; I.R. (KBr, cm-1): 1660
(C=O, stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1270 (C–O, stretch), 1130 (C–N,
% Yield: 77 %; mp: 64–66 °C; I.R. (KBr, cm-1): 1660
(C=O, stretch), 1635 (C=N, stretch), 1595 (C=C, aromatic
stretch), 1565 (NO2, asymmetric stretch), 1380 (NO2,
symmetric stretch), 1270 (C–O, stretch), 1130 (C–N,
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stretch); H NMR (CDCl3, 300 MHz, d, TMS = 0): 8.24
stretch); H NMR (CDCl3, 300 MHz, d, TMS = 0): 7.52
(2H, d, J = 8.4 Hz), 7.54 (3H, m), 7.04 (2H, s), 6.80 (3H,
m), 5.78 (2H, s), 5.50 (1H, dd, J = 4.2 and 11.4 Hz), 5.09
(2H, s), 3.84 (6H, s), 3.83 (3H, s), 3.79 (3H, s), 3.70 (1H,
dd, J = 11.4 and 17.7 Hz), 3.10 (1H, dd, J = 4.2 and
17.7 Hz), 2.32 (3H, s); Anal. Calcd for C31H32N6O8: C,
(4H, m), 7.93 (1H, s), 7.63 (2H, d, J = 8.7 Hz), 7.52 (2H,
d, J = 8.7 Hz), 7.01 (1H, d, J = 8.1 Hz), 6.80 (1H, s), 6.61
(1H, d, J = 8.4 Hz), 5.76 (2H, s), 5.48 (1H, dd, J = 4.2
and 11.4 Hz), 5.07 (2H, s), 4.02 (1H, dd, J = 11.4 and
17.7 Hz), 3.70 (3H, m), 3.10 (1H, dd, J = 4.2 and
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