Hussaini et al.
1H), 5.38 (d, J = 9.1 Hz, 2H), 5.30 (d, J = 3.0 Hz, 2H),
3.92 (s, 6H), 3.89 (s, 3H), 3.87 (s, 3H), 3.80 (s, 3H), 3.71
(dd, J = 11.9, 5.4 Hz, 1H), 3.09 (dd, J = 13.0, 4.5 Hz,
1H), 2.44 (s, 3H); ESI-MS: 618 [M + H]+; HRMS Calcd for
C32H35N5O8 [M + H]+618.2519 Found: 618.2496.
1-(5-(3-((1-(3-Amino-4-methoxybenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)-4-methoxyphenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12l)
Yield: 86%; M.P: 211–213 °C;1H NMR (300 MHz, CDCl3): d
7.52 (s, 1H), 6.97 (s, 2H), 6.89 (s, 1H), 6.80 (s, 2H), 6.70 (d,
J = 8.1 Hz, 1H), 6.62 (dd, J = 6.4, 1.8 Hz, 1H), 6.54 (d,
J = 1.8 Hz, 1H), 5.52 (dd, J = 7.4, 4.3 Hz, 1H), 5.33 (s,
2H), 5.22 (s, 2H), 3.92 (s, 6H), 3.89 (s, 3H), 3.83 (s,3H), 3.79
(s,3H), 3.69 (dd, J = 11.9, 5.6 Hz, 1H), 3.12 (dd, J = 13.2,
4.3 Hz, 1H), 2.42 (s, 3H); ESI-MS: 617 [M + H]+; HRMS
Calcd for C32H36N6O7 [M + H]+617.2679 Found: 617.2645.
1-(5-(3-((1-(4-Fluoro-3-methoxybenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)-4-methoxyphenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12i)
Yield: 88%; M.P: 199–201 °C;1H NMR (500 MHz, CDCl3):
d 7.56 (s, 1H), 7.03 (dd, J = 8.0, 3.0 Hz, 1H), 6.96 (s, 2H),
6.88–6.86 (m, 2H), 6.81 (s, 3H), 5.50 (dd, J = 8.0, 4.0 Hz,
1H), 5.43 (s, 2H), 5.24 (s, 2H), 3.91 (s, 6H), 3.89 (s, 3H),
3.83 (s, 3H), 3.79 (s, 3H), 3.69 (dd, J = 12.0, 5.0 Hz, 1H),
3.12 (dd, J = 13.0, 4.5 Hz, 1H), 2.41 (s, 3H); 13C NMR
(75 MHz, CDCl3): d 168.7, 153.7, 153.3, 149.1, 148.1,
147.5, 144.4, 140.2, 134.4, 130.8, 126.7, 122.9, 120.5,
118.8, 116.4, 116.2, 113.3, 112.4, 112.0, 103.9, 63.2,
60.8, 59.5, 56.2, 55.8, 53.6, 42.4, 21.9.; ESI-MS: 620
1-(5-(3-((1-(3-Chloro-4-fluorobenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)-4-methoxyphenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12m)
Yield: 90%; M.P: 195–197 °C;1H NMR (300 MHz, CDCl3):
d7.61 (s, 1H), 7.34 (d, J = 6.2 Hz, 1H), 7.15–7.12 (m, 2H),
6.97 (s, 2H), 6.88 (s, 1H), 6.82 (s, 2H), 5.51 (dd, J = 7.2,
4.4 Hz, 1H), 5.45 (s, 2H), 5.26 (s, 2H), 3.92 (s, 6H), 3.89 (s,
3H), 3.80 (s,3H), 3.72 (dd, J = 12.0, 5.6 Hz, 1H), 3.14 (dd,
J = 13.0, 4.5 Hz, 1H), 2.41 (s, 3H); 13C NMR (100 MHz,
CDCl3): d 168.7, 153.8, 153.3, 149.2, 147.5, 144.5, 140.2,
134.4, 130.4, 128.0, 126.7, 123.1, 118.8, 117.3, 117.1,
112.7, 112.1, 103.9, 63.2, 60.9, 59.6, 56.2, 55.9, 52.8,
42.4, 22.0; ESI-MS: 624 [M + H]+; HRMS Calcd for
C31H31ClFN5O6 [M + H]+624.1980 Found: 624.1957.
[M + H]+;
[M + H]+620.2476 Found: 620.2442.
HRMS
Calcd
for
C32H34FN5O7
1-(5-(3-((1-(3-Fluoro-4-methoxybenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)-4-methoxyphenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12j)
Yield: 87%; M.P: 205–207 °C;1H NMR (300 MHz, CDCl3): d
7.57 (s, 1H), 7.09 (s, 1H), 6.99–6.95 (m, 3H), 6.92 (s, 1H),
6.89 (s, 1H), 6.81 (s, 2H), 5.50 (dd, J = 7.4, 4.3 Hz, 1H),
5.40 (s, 2H), 5.24 (s, 2H), 3.92 (s, 6H), 3.88 (d, J = 3.4 Hz,
6H), 3.79 (s, 3H), 3.72 (dd, J = 11.8, 5.6 Hz, 1H), 3.12 (dd,
J = 13.0, 4.5 Hz, 1H), 2.42 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 168.7, 153.7, 153.3, 149.1, 147.4, 144.3, 140.1,
134.3, 127.2, 126.7, 124.2, 122.9, 118.8, 116.1, 115.9,
113.6, 112.4, 111.9, 103.8, 63.2, 60.9, 59.5, 56.2, 55.8,
53.2, 42.4, 21.9; ESI-MS: 620 [M + H]+; HRMS Calcd for
C32H35FN5O7 [M + H]+620.2515 Found: 620.2504.
1-(5-(4-Methoxy-3-((1-(3-nitrobenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)phenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12n)
Yield: 78%; M.P: 205–207 °C;1H NMR (300 MHz, CDCl3): d
8.25–8.17 (m, 2H), 7.69 (s, 1H), 7.61–7.52 (m, 2H), 6.97 (s,
2H), 6.88 (s, 1H), 6.82 (s, 2H), 5.60 (s, 2H), 5.49 (dd,
J = 7.2, 4.5 Hz, 1H), 5.28 (s, 2H), 3.92 (d, J = 8.4 Hz, 9H),
3.79 (s, 3H), 3.73 (dd, J = 11.9, 5.8 Hz, 1H), 3.14 (dd,
J = 13.2, 4.3 Hz, 1H), 2.41 (s, 3H); 13C NMR (125 MHz,
CDCl3): d 168.7, 153.3, 149.1, 148.4, 147.1, 144.6, 140.1,
136.6, 134.4, 133.9, 130.1, 126.7, 123.6, 123.4, 122.9,
118.8, 112.8, 112.1, 103.8, 63.1, 60.9, 59.6, 56.2, 55.8,
53.0, 42.4, 22.0; ESI-MS: 617 [M + H]+; HRMS Calcd for
1-(5-(4-Methoxy-3-((1-(4-methoxy-3-nitrobenzyl)-
1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12k)
C
31H32N6O8 [M + H]+617.2282 Found: 617.2305.
Yield: 85%, M.P: 205–207 °C;1H NMR (300 MHz, CDCl3):
d7.83 (d, J = 1.5 Hz, 1H), 7.67 (s, 1H), 7.46 (dd, J = 6.8,
1.5 Hz, 1H), 7.08 (d, J = 9.1 Hz, 1H), 6.97 (s, 2H), 6.88
(bs, 1H), 6.82 (s, 2H), 5.50 (d, J = 4.5 Hz, 1H), 5.49 (s,
2H), 5.27 (s, 2H), 3.96 (s, 3H), 3.92 (s, 6H), 3.89 (s,3H),
3.80 (s,3H) 3.71 (dd, J = 11.3, 5.3 Hz, 1H), 3.13 (dd,
J = 13.6, 4.5 Hz, 1H), 2.42 (s, 3H); 13C NMR (100 MHz,
CDCl3): d 168.8, 158.8, 153.7, 149.2, 147.2, 140.2,
139.5, 134.4, 133.9, 126.9, 126.7, 125.5, 118.8, 114.3,
112.9, 112.2, 103.9, 60.9, 59.6, 56.7, 56.2, 55.9, 42.5,
22.0; ESI-MS: 647 [M + H]+; HRMS Calcd for C32H34N6O9
[M + H]+647.2421 Found: 647.2399.
1-(5-(3-((1-(3-Aminobenzyl)-1H-1,2,3-triazol-4-yl)
methoxy)-4-methoxyphenyl)-3-(3,4,5-
trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
ethanone (12o)
Yield: 82%; M.P: 210–212 °C;1H NMR (300 MHz, CDCl3):
d 7.63 (s, 1H), 7.04 (t, J = 7.5 Hz, 1H), 6.96 (s, 2H), 6.90
(s, 1H), 6.76 (s, 3H), 6.68 (d, J = 7.5 Hz, 2H), 5.51 (dd,
J = 7.5, 4.5 Hz, 1H), 5.31 (s, 2H), 5.18 (s, 2H), 3.91 (s,
6H), 3.88 (s, 3H), 3.73 (s,3H), 3.66 (dd, J = 11.3, 5.3 Hz,
1H), 3.10 (dd, J = 12.8, 4.5 Hz, 1H), 2.40 (s, 3H); 13C
102
Chem Biol Drug Des 2016; 88: 97–109