T. Chandra et al. / European Journal of Medicinal Chemistry 45 (2010) 1772–1776
1775
130.1, 129.6, 128.9, 125.1, 120.2, 117.4, 104.2, 35.2, 20.2.; Anal. Calcd
6.1.17. 1-(2-0Chloroacridin-90-yl)-3-(bromomethyl)-pyrazol-5-
for C17H12N3OCl: C, 65.92; H, 3.90; N, 13.57; Found: C, 65.80; H,
one (14)
3.76; N, 13.72%; MS: [M]þ at m/z 309.07.
Yield (74%), (Acetone), m.p:185 ꢂC; IR (KBr) nmax in cmꢁ1: 3055
(C–H of aromatic), 2946 (C–H of aliphatic), 1714 (C]O), 1612
(C]N), 1545 (C]C of aromatic ring), 1283 (N–N), 612 (C–Br); 1H
6.1.11. 1-(20-Methoxyacridin-90-y)l-3-methyl pyrazol-5-one (9)
Yield (57%), (Methanol), m.p: 231–232 ꢂC; IR (KBr) nmax in
cmꢁ1: 3050 (C–H of aromatic), 2945 (C–H of aliphatic), 1715
(C]O), 1612 (C]N), 1544 (C]C of aromatic ring), 1285 (N–N); 1H
NMR (CDCl3)
d
in ppm : 7.75 (m, 7H, Ar–H), 3.42 (s, 2H, CH2CO), 2.52
ppm: 168.0, 155.7, 149.6, 148.4,
(s, 2H, CH2Br); 13C NMR (CDCl3)
d
132.3, 130.4, 130.0, 129.5, 128.8, 125.2, 120.2, 117.5, 37.4, 31.2.; Anal.
Calcd for C17H11N3OBrCl: C, 52.54; H, 2.85; N, 10.81; Found: C,
52.44; H, 2.65; N, 10.65%; MS: [M]þ at m/z 388.65.
NMR (CDCl3)
d
in ppm : 7.78 (m, 7H, Ar–H), 3.71(s, 3H, OCH3), 3.41
ppm: 168.5,
(s, 2H, CH2CO), 2.54 (s, 3H, CH3); 13C NMR (CDCl3)
d
158.1,155.2, 150.4, 149.5, 148.2, 130.5, 129.5, 128.6, 125.2, 122.2,
120.4, 117.7, 105.3, 56.2, 35.5, 20.; Anal. Calcd for C18H15N3O2: C,
70.81; H, 4.94; N, 13.76; Found: C, 70.92; H, 4.84; N, 13.62%; MS:
[M]þ at m/z 305.33.
6.1.18. 1-(20-Methoxyacridin-90-yl)-3-(bromomethyl)-pyrazol-5-
one (15)
Yield 71% (Methanol): m.p 192 ꢂC. IR (KBr) nmax in cmꢁ1: 3052
(C–H of aromatic), 2944 (C–H of aliphatic),1716 (C]O),1615 (C]N),
1544 (C]C of aromatic ring), 1280 (N–N), 615 (C–Br); 1H NMR
6.1.12. 1-(20-Bromoacridin-90-y)l-3-methyl pyrazol-5-one (10)
Yield (60%), (Ethyl acetate), m.p:241 ꢂC; IR (KBr) nmax in cmꢁ1
:
(CDCl3)
d
in ppm : 7.72 (m, 7H, Ar–H), 3.73 (s, 3H, OCH3), 3.40 (s, 2H,
ppm: 168.1, 158.2,
3052 (C–H of aromatic), 2948 (C–H of aliphatic), 1718 (C]O), 1614
CH2CO), 2.54 (s, 2H, CH2Br); 13C NMR (CDCl3)
d
(C]N), 1543 (C]C of aromatic ring), 1282 (N–N); 1H NMR (CDCl3)
155.5, 150.2, 149.7, 148.6, 130.6, 129.5, 128.7, 125.0, 122.4, 117.8,
105.3, 56.2, 37.6, 31.4.; Anal. Calcd for C18H14N3O2Br: C, 56.27; H,
3.67; N, 10.94; Found: C, 56.38; H, 3.56; N, 10.84%. MS: [M]þ at m/z
383.03.
d
in ppm: 7.79 (m, 7H, Ar–H), 3.43 (s, 2H, CH2CO), 2.52 (s, 3H, CH3);
13C NMR (CDCl3)
d
ppm: 168.1,155.4,150.3,149.6,148.8,132.4,130.7,
129.4, 128.8, 125.0, 120.2, 120.0, 117.5, 35.4, 20.1.; Anal. Calcd for
C17H12N3OBr: C, 57.65; H, 3.41; N, 11.86; Found: C,57.82; H, 3.34; N,
11.72%; MS: [M]þ at m/z 354.20.
6.1.19. 1-(20-Bromoacridin-90-yl)-3-(bromomethyl)-pyrazol-5-
one (16)
6.1.13. 1-(40-Chloro-20-methoxyacridin-90-y)l-3-methyl pyrazol-5-
Yield (65%), (Methanol), m.p: 176 ꢂC; IR (KBr) nmax in cmꢁ1: 3054
(C–H of aromatic), 2946 (C–H of aliphatic), 1714 (C]O), 1612
(C]N), 1546 (C]C of aromatic ring), 1282 (N–N), 616 (C–Br); 1H
one (11)
Yield (53%), (DMF/Water), m.p:247 ꢂC; IR (KBr) nmax in cmꢁ1
:
3055 (C–H of aromatic), 2952 (C–H of aliphatic), 1720 (C]O), 1615
NMR (CDCl3)
d
in ppm : 7.70 (m, 7H, Ar–H), 3.42 (s, 2H, CH2CO), 2.52
ppm: 168.0, 155.6, 150.5, 149.4,
(C]N), 1545 (C]C of aromatic ring), 1285 (N–N); 1H NMR (CDCl3)
(s, 2H, CH2Br); 13C NMR (CDCl3)
d
d
in ppm : 7.83 (m, 6H, Ar–H), 3.74 (s, 3H, OCH3),3.45 (s, 2H,
148.7, 130.7, 129.6, 128.9, 125.3, 120.2, 117.7, 104.2, 37.5, 31.8.; Anal.
Calcd for C17H11N3OBr2: C, 47.14; H, 2.56; N, 9.70; Found: C, 47.28;
H, 2.46; N, 9.84%; MS: [M]þ at m/z 430.93.
CH2CO), 2.55 (s, 3H, CH3); 13C NMR (CDCl3)
d
ppm: 168.3, 157.6,
155.5, 150.4, 149.3, 148.6, 134.4, 129.7, 128.9, 125.3, 122.2, 120.4,
117.7, 56.1, 35.2, 20.; Anal. Calcd for C18H14N3O2Cl: C, 63.63; H,
4.15; N, 12.37; Found: C, 63.46; H, 4.06; N, 12.47%. MS: [M]þ at m/z
339.78.
6.1.20. 1-(40-Chloro-20-methoxyacridin-90-yl)-3-(bromomethyl)-
pyrazol-5-one (17)
Yield (62%), (Ethanol), m.p: 210 ꢂC; IR (KBr) nmax in cmꢁ1: 3056
(C–H of aromatic), 2944 (C–H of aliphatic), 1716 (C]O), 1615
(C]N), 1548 (C]C of aromatic ring), 1285 (N–N), 614 (C–Br); 1H
6.1.14. 1-(20, 40-Dichloroacridin-90-yl)-3-methyl pyrazol-5-one (12)
Yield (50%), (Acetone), m.p: 255 ꢂC; IR (KBr) nmax in cmꢁ1: 3056
(C–H of aromatic), 2953 (C–H of aliphatic), 1722 (C]O), 1616
(C]N), 1548 (C]C of aromatic ring), 1288 (N–N); 1H NMR (CDCl3)
NMR (CDCl3)
d
in ppm : 7.72 (m, 6H, Ar–H), 3.75 (s, 3H, OCH3), 3.40
ppm: 168.4,
(s, 2H, CH2CO), 2.54 (s, 2H, CH2Br); 13C NMR (CDCl3)
d
d
in ppm: 7.85 (m, 6H, Ar–H), 3.46 (s, 2H, CH2CO), 2.56 (s, 3H, CH3);
155.7, 150.3, 149.7, 148.6, 134.5, 129.5, 128.7, 125.0, 120.4, 117.8,
104.2, 37.5, 31.6.; Anal. Calcd for C18H13N3O2BrCl: C, 51.64; H, 3.13;
N, 10.04; Found: C, 51.48; H, 3.26; N, 10.14%. MS: [M]þ at m/z
418.67.
13C NMR (CDCl3)
d
ppm: 168.1, 155.6, 150.4, 149.6, 148.5, 134.7, 131.5,
130.5, 129.7, 128.8, 125.3, 120.2, 120.0, 117.6, 35.6, 20.2.; Anal. Calcd
for C17H11N3OCl2: C, 59.32; H, 3.22; N, 12.21; Found: C, 59.46; H,
3.26; N, 12.06%. MS: [M]þ at m/z 344.19.
6.1.21. 1-(20, 40-Dichloroacridin-90-yl)-3-(bromomethyl)-pyrazol-5-
6.1.15. General procedure for the synthesis of 1-(20,40-di substituted
acridin-90-yl)-3-(bromomethyl)-pyrazol-5-ones (13–18)
one (18)
Yield (68%), (DMF/Water), m.p: 207 ꢂC; IR (KBr) nmax in cmꢁ1
:
The compounds 13–18 were synthesized by adding solution of
bromine (0.02 mol) in acetic acid drop wise with constant stirring
in the cold solution of compounds 7–12 (0.01 mol). The reaction
mixture was distilled off and the residue thus obtained was washed
with water, filtered, dried and recrystallized with appropriate
solvent to give compounds 13–18.
3054 (C–H of aromatic), 2946 (C–H of aliphatic), 1720 (C]O), 1616
(C]N), 1550 (C]C of aromatic ring), 1286 (N–N), 615 (C–Br); 1H
NMR (CDCl3)
d
in ppm : 7.70 (m, 6H, Ar–H), 3.42 (s, 2H, CH2CO), 2.56
ppm: 168.0, 155.9, 150.5, 149.1,
(s, 2H, CH2Br);13C NMR (CDCl3)
d
148.4, 134.6, 129.6, 128.9, 125.2, 120.3, 117.7, 104.4, 37.6, 31.5.; Anal.
Calcd for C17H10N3OBrCl2: C, 48.26; H, 2.38; N, 9.93; Found: C,
48.38; H, 2.16; N, 9.80%; MS: [M]þ at m/z 423.09.
6.1.16. 1-(Acridin-90-yl)-3-(bromomethyl)-pyrazol-5-one (13)
Yield (72%), m.p:201 ꢂC. IR (KBr) nmax in cmꢁ1: 3052 (C–H of
aromatic), 2945 (C–H of aliphatic), 1712 (C]O), 1610 (C]N), 1542
(C]C of aromatic ring), 1281 (N–N), 610 (C–Br); 1H NMR (CDCl3)
6.1.22. General procedure for the synthesis of 1-(20,40-di substituted
acridin-90-yl)-3-(50-pyridin-4-yl)-(1,3,4 oxadizol-2-yl-thiomethyl)-
pyrazol-5-one (19–24)
d
in ppm : 7.74 (m, 8H, Ar–H), 3.40 (s, 2H, CH2CO), 2.55 (s, 2H,
The solution of 13–18 (0.01 mol) in pyridine (80 mL) and 5-(4-
pyridinyl)-1,3,4-oxadiazole-2-thiol (0.01 mol) were refluxed for
5 h. The reaction mixture was concentrated and poured it crushed
ice. The separated solid was filtered, dried and recrystallized with
appropriate solvent to give compounds 19–24.
CH2Br); 13C NMR (CDCl3)
d
ppm: 168.0, 155.5, 149.7, 149.4, 129.4,
129.0, 125.5, 123.7, 37.6, 31.5.; Anal. Calcd for C17H12N3OBr: C, 57.65;
H, 3.41; N,11.86; Found: C, 57.55; H, 3.55; N,11.75%; MS: [M]þ at m/z
354.20.