174
B. K. Ghotekar et al.
8-Chloro-1,2-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one
(7a, C10H6ClN3O)
2,800, 1,691, 1,615, 1,529, 1,455, 1,369, 1,104, 781,
585 cm-1 1H NMR (300 MHz, DMSO-d6): d = 7.19–
;
Yield 1.66 g (76%); m.p.: 356 °C (DMF); Rf = 0.70
(toluene–acetone 8:2); IR (KBr): vꢀ ¼ 3;400; 3,310, 3,091,
2,925, 2,853, 1,692, 1,612, 1,527, 1,459, 1,336, 1,295,
;
1,095, 813, 720, 621, 551 cm-1 1H NMR (300 MHz,
7.78 (m, 5H, Ar–H), 8.20–8.35 (m, 3H, Ar–H), 8.78 (s, 1H,
C4–H), 12.08 (bs, 1H, NH) ppm; 13C NMR (75 MHz,
DMSO-d6): d = 120.8, 121.2, 126.5, 126.9, 127.8, 129.5,
130.9, 131.9, 132.1, 134.7, 139.1, 141.5, 145.0, 148.6 ppm.
DMSO-d6): d = 7.60–7.96 (m, 3H, Ar–H), 8.50 (s,1H,
C4–H), 11.43 (bs, 1H, NH), 12.49 (bs, 1H, NH) ppm; 13C
NMR (75 MHz, DMSO-d6): d = 121.9, 126.0, 127.0,
130.5, 131.5, 132.3, 138.1, 145.0, 148.6, 155.4 ppm; MS
(70 eV): m/z = 221 ([M ? 2]?), 219 (M?), 206, 190, 176,
162, 152, 137, 126, 99, 98, 74, 63, 50, 38.
8-Bromo-1,2-dihydro-2-(2-hydroxyethyl)-3H-pyrazolo
[4,3-c]quinolin-3-one (7f, C12H10BrN3O2)
Yield 2.24 g (73%); m.p.: 304 °C (DMF); Rf = 0.74
(toluene–acetone 9:1); IR (KBr): vꢀ ¼ 3;400; 3,175, 3,095,
2,901, 1,690, 1,615, 1,554, 1,514, 1,460, 1,377, 1,355,
1,298, 1,185, 1,151, 1,108, 1,021, 959, 869, 825, 810, 645,
1
8-Chloro-1,2-dihydro-2-phenyl-3H-pyrazolo[4,3-c]quino-
lin-3-one (7b, C16H10ClN3O)
605 cm-1; H NMR (300 MHz, DMSO-d6): d = 2.45 (bs,
1H, OH), 3.96 (t, J = 7 Hz, 2H, CH2), 4.09 (t, J = 7 Hz,
2H, OCH2), 7.65–8.10 (m, 3H, Ar–H), 8.93 (s, 1H, C4–H),
11.55 (bs, 1H, NH) ppm; 13C NMR (75 MHz, DMSO-d6):
d = 58.2, 62.1, 122.1, 126.6, 128.1, 130.8, 131.9, 132.8,
135.2, 138.2, 145.0, 149.2 ppm.
Yield 2.30 g (78%); m.p.: 368 °C (DMF); Rf = 0.61
(toluene–acetone 8:2); IR (KBr): vꢀ ¼ 3;422; 3,091, 2,852,
2,800, 1,694, 1,619, 1,527, 1,450, 1,360, 1,104, 784,
;
581 cm-1 1H NMR (300 MHz, DMSO-d6): d = 7.14–
7.71 (m, 5H, Ar–H), 8.15–8.20 (m, 3H, Ar–H), 8.75 (s, 1H,
C4-H), 12.20 (bs, 1H, NH) ppm; 13C NMR (75 MHz,
DMSO-d6): d = 120.2, 121.6, 126.0, 126.3, 127.3, 129.4,
130.5, 131.5, 132.3, 134.6, 139.7, 141.0, 145.0, 148.6 ppm;
MS (70 eV): m/z = 297 ([M ? 2]?), 295 (M?), 294, 268,
266, 238, 215, 204, 189, 176, 162, 147, 126, 98, 77, 63, 51,
39.
Acknowledgments The authors thank the University Grants Com-
mission (UGC), New Delhi, India, for financial support and Professor
D.D. Dhavale, Department of Chemistry, University of Pune, India
for his encouragement and useful discussion.
References
8-Chloro-1,2-dihydro-2-(2-hydroxyethyl)-3H-pyrazol-
o[4,3-c]quinolin-3-one (7c, C12H10ClN3O2)
1. Michael J (1997) Nat Prod Rep 14:605
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Chem 46:138
Yield 1.89 g (72%); m.p.: 323 °C (DMF); Rf = 0.72
(toluene–acetone 8:2); IR (KBr): vꢀ ¼ 3;395; 3,153, 3,091,
2,903, 1,695, 1,618, 1,554, 1,524, 1,469, 1,379, 1,359,
1,295, 1,188, 1,151, 1,105, 1,031, 957, 866, 825, 800, 645,
1
605 cm-1; H NMR (300 MHz, DMSO-d6): d = 2.40 (bs,
1H, OH), 3.92 (t, J = 7 Hz, 2H, CH2), 4.01 (t, J = 7 Hz,
2H, OCH2), 7.62-7.98 (m, 3H, Ar–H), 8.81 (s, 1H, C4–H),
11.90 (bs, 1H, NH) ppm; 13C NMR (75 MHz, DMSO-d6):
d = 57.4, 61.5, 121.9, 126.0, 127.0, 130.5, 131.5, 132.3,
134.6, 138.0, 145.0, 148.6 ppm.
7. Gorlitzer K, Bode M, Jones P, Jomaa H, Wiesner J (2007)
Pharmazie 62:15
8. Penning T, Talley J, Bertenshaw S, Carter J, Colins P, Graneton J,
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11. Kidwai M, Negi N (1997) Monatsh Chem 128:85
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Lett 15:73
8-Bromo-1,2-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one
(7d, C10H6BrN3O)
Yield 1.95 g (74%); m.p.: 338 °C (DMF); Rf = 0.68
(toluene–acetone 8:2); IR (KBr): vꢀ ¼ 3;420; 3,330, 3,096,
2,925, 2,850, 1,690, 1,612, 1,527, 1,459, 1,366, 1,294,
;
1,095, 813, 710, 631, 541 cm-1 1H NMR (300 MHz,
DMSO-d6): d = 7.65–7.94 (m, 3H, Ar–H), 8.45 (s, 1H, C4-
H), 11.48 (bs, 1H, NH), 12.52 (bs, 1H, NH) ppm; 13C NMR
(75 MHz, DMSO-d6): d = 121.2, 126.5, 127.8, 131.1,
131.9, 133.1, 139.1, 146.2, 149.2, 156.2 ppm.
16. Suresh T, Nandha Kumar R, Magesh S, Mohan P (2003) Ind J
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17. Suresh T, Nandha Kumar R, Magesh S, Mohan P (2003) Ind J
Chem 42B:688
8-Bromo-1,2-dihydro-2-phenyl-3H-pyrazolo[4,3-c]quino-
lin-3-one (7e, C16H10BrN3O)
Yield 2.61 g (77%); m.p.: 320 °C (DMF); Rf = 0.63
(toluene–acetone 8:2); IR (KBr): vꢀ ¼ 3;433; 3,096, 2,848,
18. Dlugosz A, Dus D (1996) Farmaco 51:367
19. Selvi S, Nadaraj V, Mohan S, Sasi R, Hema M (2006) 14:3896
123