Sobhani et al.
803
3
3
(3H, s, CH3), 2.31 (3H, s, CH3), 4.42 (1H, t, JHH = 8.0 Hz,
(3H, s, CH3), 4.91 (1H, t, JHH = 8.0 Hz, CH), 5.32 (2H,
3
3
3
3
CH), 4.81 (1H, dd, JHH = 12.8 Hz, JHH = 6.8 Hz, CH2),
dd, JHH = 8.8 Hz, JHH = 6.8 Hz, CH2), 6.97 (1H, dd,
3JHH = 6.6 Hz, JHH = 3.6 Hz, Ar), 7.11 (1H, d, JHH
3
3
3
3
5.20 (1H, dd, JHH = 12.0 Hz, JHH = 9.6 Hz, CH2), 7.06
=
3
3
(3H, d, JHH = 8.0 Hz, Ar), 7.13 (2H, t, JHH = 7.2 Hz, Ar),
3
6.8 Hz, Ar), 7.22 (1H, t, JHH = 7.2 Hz, Ar), 7.39 (1H, d,
3
3
7.20 (2H, d, JHH = 8.0 Hz, Ar), 7.30 (2H, d, JHH = 8 Hz,
Ar), 10.9 (1H, br s, OH). 13C NMR (100 MHz, CDCl3) dC:
10.6, 21.0, 39.3, 76.8, 103.4, 120.7, 125.6, 127.4, 128.8,
129.5, 135.6, 136.2, 136.5, 137.1, 146.9. MS m/z (%): 337
(3.6), 118 (100), 42 (30.0); Anal. calcd for C19H19N3O3
(337.14) (%): C 67.64, H 5.68, N 12.46; found: C 67.54, H
5.71, N 12.39.
3JHH = 5.2 Hz, Ar), 7.45 (2H, t, JHH = 8.0 Hz, Ar), 7.71
3
(2H, d, JHH = 8.2 Hz, Ar), 11.35 (1H, br s, OH). 13C NMR
3
(100 MHz, CDCl3) dC: 11.1, 34.3, 77.3, 103.8, 119.0, 121.2,
125.4, 127.4, 129.4, 137.3, 143.0, 148.2, 162.4. Anal. calcd
for C16H15N3O3 S (329.08) (%): C 58.34, H 4.59, N 12.76;
found: C 58.25, H 4.50, N 12.69.
Acknowledgments
3-Methyl-4-[2-nitro-1-(4-chlorophenyl)ethyl]-1-phenyl-5-
pyrazolone (3d)
We are thankful to Birjand University Research Council
for their support of this work.
White solid; yield: 95%, 0.34 g; mp 155–156 °C. IR (nmax
,
1
cm–1): 2900 (O–H). H NMR (400 MHz, CDCl3) dH: 1.91
3
References
(3H, s, CH3), 4.39 (1H, t, JHH = 7.6 Hz, CH), 4.78 (1H,
3
3
dd, JHH = 13.0 Hz, JHH = 6.8 Hz, CH2), 5.12 (1H, dd,
(1) McDonald, E.; Jones, K.; Brough, P. A.; Drysdale, M. J.;
Workman, P. Curr. Top. Med. Chem. 2006, 6 (11), 1193.
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(2) Elguero, J. In Comprehensive Heterocyclic Chemistry II;
Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.;
Pergamon: Oxford, 1996; Vol. 5.
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as Drugs: Facts and Fantasies. In Targets in Heterocyclic
Systems; Attanasi, O. A.; Spinelli, D., Eds.; Italian Society of
Chemistry: Roma, 2002; Vol. 6, pp 52–98.
(4) Park, H.-J.; Lee, K.; Park, S.-J.; Ahn, B.; Lee, J.-C.; Cho, H.
Y.; Lee, K.-I. Bioorg. Med. Chem. Lett. 2005, 15 (13), 3307.
doi:10.1016/j.bmcl.2005.03.082.
(5) Clark, M. P.; Laughlin, S. K.; Laufersweiler, M. J.; Bookland,
R. G.; Brugel, T. A.; Golebiowski, A.; Sabat, M. P.; Townes, J.
A.; Vanrens, J. C.; Djung, J. F.; Natchus, M. G.; De, B.; Hsieh,
L. C.; Xu, S. C.; Walter, R. L.; Mekel, M. J.; Heitmeyer, S. A.;
Brown, K. K.; Juergens, K.; Taiwo, Y. O.; Janusz, J. M. J.
Med. Chem. 2004, 47 (11), 2724. doi:10.1021/jm049968m.
(6) Cho, I. H.; Noh, J. Y.; Park, S. W.; Ryu, H. C.; Lim, J. W.;
Kim, J. H.; Chae, M. Y.; Kim, D. H.; Jung, H. S.; Park, H. J.;
Kim, Y. H.; Min, I. K. US Patent 2,004,002, 2004; p 532.
(7) Clark, M. P.; Laughlin, S. K.; Golebiowski, A.; Brugel, T. A.;
Sabat, M. WO Patent 2005047, 2005; p 287.
(8) Kakiuchi, Y.; Sasaki, N.; Satoh-Masuoka, M.; Murofushi, H.;
Murakami-Murofushi, K. Biochem. Biophys. Res. Commun.
2004, 320 (4), 1351. doi:10.1016/j.bbrc.2004.06.094.
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(11), 1617. doi:10.1517/13543776.15.11.1617.
3JHH = 12.6 Hz, JHH = 8.8 Hz, CH2), 7.12 (1H, d, JHH
=
3
3
3
8.0 Hz, Ar), 7.15 (3H, t, JHH = 6.8 Hz, Ar), 7.17–7.28 (5H,
m, Ar), 11.10 (1H, br s, OH). 13C NMR (100 MHz, CDCl3)
dC: 10.5, 14.2, 39.0, 76.5, 120.9, 126.3, 128.9, 129.0, 129.1,
129.3, 133.3, 136.9, 137.7, 146.7. MS m/z (%): 358 (3.3),
360 (1.1), 139 (3.3), 141 (1.1), 42 (CNO, 100). Anal. calcd
for C18H16ClN3O3 (357.09) (%): C 60.42, H 4.51, N 11.74;
found: C 60.51, H 4.55, N 11.81.
3-Methyl-4-[2-nitro-1-(4-nitrophenyl)ethyl]-1-phenyl-5-
pyrazolone (3e)
White solid; yield: 94%, 0.34 g; mp 176–180 °C. IR (nmax
,
1
cm–1): 2832 (O–H). H NMR (400 MHz, CDCl3) dH: 2.24
3
(3H, s, CH3), 4.65 (1H, t, JHH = 7.2 Hz, CH), 5.08 (1H, dd,
3
3
3JHH = 13.4 Hz, JHH = 7.2 Hz, CH2), 5.41 (1H, dd, JHH
=
3
3
13.2 Hz, JHH = 8.8 Hz, CH2), 7.22 (1H, t, JHH = 7.2 Hz,
Ar), 7.38 (2H, t, JHH = 7.6 Hz, Ar), 7.55 (2H, d, JHH
3
3
=
3
3
7.6 Hz, Ar), 7.7 (2H, d, JHH = 8.8 Hz, Ar), 8.2 (2H, d, JHH
= 8.4 Hz, Ar). 13C NMR (100 MHz, CDCl3) dC: 11.3, 39.7,
75.9, 120.0, 124.2, 124.4, 126.2, 128.8, 129.0, 129.3, 136.0,
146.2, 147.3, 148.4. MS m/z: 368 (1.2), 149 (2.9), 42 (100).
Anal. calcd for C18H16N4O5 (368.11) (%): C 58.69, H 4.38, N
15.21; found: C 58.71, H 4.44, N 15.11.
3-Methyl-4-[2-nitro-1-(4-bromophenyl)ethyl]-1-phenyl-5-
pyrazolone (3f)
White solid; yield: 95%, 0.38 g; mp 169–170 °C. IR (nmax
,
(10) Ishida, M. WO Patent 2006212, 2006.
(11) Speckbacher, M.; Braun, H.-J. WO Patent 2006012, 2006;
1
cm–1): 2703 (O–H). H NMR (400 MHz, CDCl3) dH: 2.18
3
3
(3H, s, CH3), 4.62 (1H, dd, JHH = 8.8 Hz, JHH = 6.8 Hz,
p 934.
3
3
CH), 5.36 (2H, dd, JHH = 8.4 Hz, JHH = 6.8 Hz, CH2),
(12) Sugiura, S.; Ohno, S.; Ohtani, O.; Izumi, K.; Kitamikado, T.;
Asai, H.; Kato, K.; Hori, M.; Fujimura, H. J. Med. Chem.
1977, 20 (1), 80. doi:10.1021/jm00211a016.
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Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazoli-
dines, Indazoles and Condensed Rings; Weissberger, A., Ed.;
Interscience Publishers: New York, 1967.
3
3
7.22 (2H,d, JHH = 8.0 Hz, Ar), 7.45 (3H, t, JHH = 6.8 Hz,
3
3
Ar), 7.53 (2H, d, JHH = 8.0 Hz, Ar), 7.70 (2H, d, JHH
=
7.6 Hz, Ar), 11.33 (1H, br s, OH). 13C NMR (100 MHz,
CDCl3) dC: 11.4, 38.6, 76.8, 103.2, 119.2, 120.7, 125.3,
129.4, 130.4, 131.9, 137.4, 139.9, 148.1. MS m/z: 401 (2.0),
403 (1.6), 226 (2.1), 228 (2.3), 173 (77.6), 76 (100). Anal.
calcd for C18H16BrN3O3 (401.04) (%): C 53.75, H 4.01, N
10.45; found: C 53.85, H 4.21, N 10.38.
(14) Rosiere, C. E.; Grossman, M. I. Science 1951, 113 (2945),
651. doi:10.1126/science.113.2945.651.
(15) Bailey, D. M.; Hansen, P. E.; Hlavac, A. G.; Baizman, E. R.;
Pearl, J.; Defelice, A. F.; Feigenson, M. E. J. Med. Chem.
1985, 28 (2), 256. doi:10.1021/jm00380a020.
(16) Mahajan, R. N.; Havaldar, F. H.; Fernandes, P. S. J. Indian
Chem. Soc. 1991, 68 (4), 245.
3-Methyl-4-[2-nitro-1-(thiophen-2-yl)ethyl]-1-phenyl-5-
pyrazolone (3g)
White solid; yield: 88%, 0.29 g; mp 124–125 °C. IR (nmax
,
1
cm–1): 2802 (O–H). H NMR (400 MHz, CDCl3) dH: 2.13
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