Med Chem Res (2012) 21:229–238
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1585 (CH=CH), 611 (C–I); 1H NMR (400 MHz, CDCl3): d
2.86 (s, 6H, N(CH3)2), 3.56 (s, 2H, CH2), 6.38–8.18 (m, 16H,
Ar–H), 6.81 (d, 1H, J = 16.6 Hz, =CHCO), 7.62 (d, 1H,
J = 16.6 Hz, =CH–Ar), 8.78 (bs, 1H, CONH), 9.16 (bs, 1H,
NH); 13C NMR (100 MHz, CDCl3): d 30.45 (CH2), 46.72
(N-(CH3)2), 111.92–150.22 (26C, CH=CH and Ar–C),
162.17 (C=O), 168.27 (C=N), 172.86 (CONH); Anal. Calcd
for C32H28IN5O2: C, 59.91; H, 4.40; N, 10.92. Found: C,
59.76; H, 4.28; N, 10.78.
6-Iodo-2-[2-(phenylamino)benzyl]-3-[5-(3-
hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl-
amino]quinazolin-4(3H)-one (6c)
Yield: 66%, m.p. 167–170°C; IR (KBr): 3550 (OH), 3452
(NH), 2927, 2855 (CH2), 1734 (C=O), 1618 (C=N), 619
;
(C–I) cm-1 1H NMR (400 MHz, CDCl3): d 3.04 (dd,
1H, Jab = 17.6 Hz, Jax = 5.6 Hz, Ha), 3.50 (dd, 1H,
Jba = 17.6 Hz, Jbx = 12.6 Hz, Hb), 3.54 (s, 2H, CH2),
5.51 (dd, 1H, Jxb = 12.6 Hz, Jxa = 5.6 Hz, Hx), 5.57 (bs,
1H, OH), 6.37–8.19 (m, 17H, NH and Ar–H), 8.39 (bs, 1H,
NH), 9.15 (bs, 1H, NH); 13C NMR (100 MHz, CDCl3): d
30.46 (CH2), 36.14 (CH2 of pyrazole), 54.98 (CH of
pyrazole), 112.28–159.51 (24C, Ar–C), 161.12 (C=N of
pyrazole), 162.24 (C=O), 168.13 (C=N); Anal. Calcd
for C30H25IN6O2: C, 57.33; H, 4.01; N, 13.37. Found:
C, 57.48; H, 4.08; N, 13.29.
General procedure for the synthesis of pyrazolyl-
quinazolin-4(3H)-ones (6a–m)
To a mixture of compound (5a) (0.01 mol) and hydrazine
hydrate (0.02 mol) in absolute methanol (30 ml) was added
a few drops of glacial acetic acid, and refluxed for 8–10 h.
After completion of the reaction, excess of solvent was
distilled off; the separated solid was filtered, washed with
water, and recrystallized from methanol.
6-Iodo-2-[2-(phenylamino)benzyl]-3-[5-(4-
hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl-
amino]quinazolin-4(3H)-one (6d)
6-Iodo-2-[2-(phenylamino)benzyl]-3-(5-phenyl-4,5-
dihydro-1H-pyrazol-3-yl-amino)quinazolin-4(3H)-one (6a)
Yield: 64%, m.p. 181–184°C; IR (KBr): 3542 (OH), 3445
(NH), 2932, 2851 (CH2), 1721 (C=O), 1612 (C=N), 612
Yield: 66%, m.p. 112–115°C; IR (KBr): 3446 (NH), 2925,
2853 (CH2), 1729 (C=O), 1615 (C=N), 617 (C–I) cm-1; 1H
NMR (400 MHz, CDCl3): d 3.03 (dd, 1H, Jab = 17.6 Hz,
(C–I) cm-1 1H NMR (400 MHz, CDCl3): d 3.08 (dd,
;
1H, Jab = 17.8 Hz, Jax = 5.6 Hz, Ha), 3.51 (dd, 1H,
Jba = 17.8 Hz, Jbx = 12.2 Hz, Hb), 3.59 (s, 2H, CH2),
5.50 (dd, 1H, Jxb = 12.2 Hz, Jxa = 5.6 Hz, Hx), 5.58 (bs,
1H, OH), 6.37–8.17 (m, 17H, NH and Ar–H), 8.37 (bs, 1H,
NH), 9.17 (bs, 1H, NH); 13C NMR (100 MHz, CDCl3): d
30.31 (CH2), 36.48 (CH2 of pyrazole), 55.26 (CH of
pyrazole), 111.92–157.37 (24C, Ar–C), 161.33 (C=N of
pyrazole), 162.06 (C=O), 167.86 (C=N); Anal. Calcd for
C30H25IN6O2: C, 57.33; H, 4.01; N, 13.37. Found: C,
57.25; H, 4.05; N, 13.28.
Jax = 5.4 Hz, Ha), 3.48 (dd, 1H, Jba = 17.6 Hz, Jbx
=
12.4 Hz, Hb), 3.54 (s, 2H, CH2), 5.49 (dd, 1H, Jxb = 12.4 Hz,
Jxa = 5.4 Hz, Hx), 6.37–8.19 (m, 18H, NH and Ar–H), 8.35
(bs, 1H, NH), 9.18 (bs, 1H, NH); 13C NMR (100 MHz,
CDCl3):d30.42(CH2), 36.32(CH2 ofpyrazole), 55.64(CHof
pyrazole), 112.37–148.76 (24C, Ar–C), 161.12 (C=N of
pyrazole), 162.19 (C=O), 168.27 (C=N); Anal. Calcd for
C30H25IN6O: C, 58.83; H, 4.11; N, 13.72. Found: C, 58.69; H,
4.18; N, 13.63.
6-Iodo-3-[5-(2-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-
yl-amino]-2-[2-(phenylamino)benzyl]quinazolin-4(3H)-
one (6e)
6-Iodo-2-[2-(phenylamino)benzyl]-3-[5-(2-
hydroxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl-
amino]quinazolin-4(3H)-one (6b)
Yield: 69%, m.p. 123–125°C; IR (KBr): 3432 (NH),
2917, 2845 (CH2), 1714 (C=O), 1617 (C=N), 748 (C–Cl),
;
629 (C–I) cm-1 1H NMR (400 MHz, CDCl3): d 3.03
Yield: 71%, m.p. 153–157°C; IR (KBr): 3546 (OH), 3440
(NH), 2921, 2848 (CH2), 1723 (C=O), 1611 (C=N), 622
1
(C–I) cm-1; H NMR (400 MHz, CDCl3): d 3.01 (dd, 1H,
(dd, 1H, Jab = 17.4 Hz, Jax = 5.4 Hz, Ha), 3.47 (dd, 1H,
Jba = 17.4 Hz, Jbx = 12.2 Hz, Hb), 3.56 (s, 2H, CH2),
5.48 (dd, 1H, Jxb = 12.2 Hz, Jxa = 5.4 Hz, Hx),
6.36–8.19 (m, 17H, NH and Ar–H), 8.42 (bs, 1H, NH),
9.15 (bs, 1H, NH); 13C NMR (100 MHz, CDCl3): d
30.14 (CH2), 36.31 (CH2 of pyrazole), 55.58 (CH of
pyrazole), 112.27–148.89 (24C, Ar–C), 161.18 (C=N of
pyrazole), 162.21 (C=O), 168.24 (C=N); Anal. Calcd for
C30H24ClIN6O: C, 55.70; H, 3.74; N, 12.99. Found: C,
55.53; H, 3.67; N, 12.88.
Jab = 17.4 Hz, Jax = 5.6 Hz, Ha), 3.45 (dd, 1H, Jba
=
17.4 Hz, Jbx = 12 Hz, Hb), 3.55 (s, 2H, CH2), 5.52 (dd,
1H, Jxb = 12 Hz, Jxa = 5.6 Hz, Hx), 6.37–8.18 (m, 17H,
NH and Ar–H), 8.41 (bs, 1H, NH), 9.15 (bs, 1H, NH),
10.34 (bs, 1H, OH); 13C NMR (100 MHz, CDCl3): d 30.67
(CH2), 35.53 (CH2 of pyrazole), 55.84 (CH of pyrazole),
111.86–155.78 (24C, Ar–C), 161.34 (C=N of pyrazole),
161.95 (C=O), 168.42 (C=N); Anal. Calcd for C30H25
IN6O2: C, 57.33; H, 4.01; N, 13.37. Found: C, 57.24; H,
3.96; N, 13.46.
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