F
C. M. Sanabria et al.
Paper
Synthesis
HRMS (ESI): m/z [M + H]+ calcd for C14H14N2OI: 353.014537; found:
353.014554.
References
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N-(4-Iodophenyl)-N′-(4-methoxyphenyl)urea (2k)23
Pale brown powder; yield: 61 mg (66% crude); mp 230 °C (dec.); Rf =
0.42 (EtOAc/hexane, 1:1).
IR (KBr): 3302, 2830, 1638, 1597, 1558, 1484, 1463, 1388, 1303, 1243,
849, 635, 500 cm–1
.
1H NMR (500 MHz, DMSO-d6): δ = 8.76 (s, 1 H), 8.56 (s, 1 H), 7.57 (d,
J = 8.6 Hz, 2 H), 7.35 (d, J = 8.9 Hz, 2 H), 7.30 (d, J = 8.6 Hz, 2 H), 6.85 (d,
J = 8.9 Hz, 2 H), 3.71 (s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 154.5, 152.6, 139.9, 137.2, 132.5,
120.4, 120.1, 114.0, 84.3, 55.2.
HRMS (ESI): m/z [M + H]+ calcd for C14H14N2O2I: 369.0095; found:
369.0107.
N-(4-Iodophenyl)-N′-(3-nitrophenyl)urea (2l)23
Yellow powder; yield: 84 mg (88%); mp 230 °C (dec.); Rf = 0.32 (EtOAc/
hexane, 1:1).
IR (KBr): 3326, 3093, 1673, 1651, 1589, 1556, 1520, 1483, 1434, 1391,
1347, 1237, 809, 629, 503 cm–1
.
1H NMR (500 MHz, DMSO-d6): δ = 9.23 (s, 1 H), 8.95 (s, 1 H), 8.51 (t,
J = 2.2 Hz, 1 H), 7.79 (ddd, J = 8.1, 2.5, 1.0 Hz, 1 H), 7.68 (ddd, J = 8.5,
2.0, 1.0 Hz, 1 H), 7.62 (d, J = 8.8 Hz, 2 H), 7.53 (t, J = 8.0 Hz, 1 H), 7.33
(d, J = 8.8 Hz, 2 H).
13C NMR (125 MHz, DMSO-d6): δ = 152.3, 148.1, 140.9, 139.2, 137.4,
(6) Khan, K. M.; Saeed, S.; Ali, M.; Gohar, M.; Zahid, J.; Khan, A.;
Perveen, S.; Choudhary, M. I. Bioorg. Med. Chem. 2009, 17, 2447.
(7) Darko, A. K.; Curran, F. C.; Copin, C.; McElwee-White, L. Tetrahe-
dron 2011, 67, 3976.
130.1, 124.4, 120.8, 116.4, 112.2, 85.1.
HRMS (ESI): m/z [M + H]+ calcd for C13H11N3O3I: 383.9840; found:
383.9843.
(8) (a) Luo, W.; Xia, M.-Y.; Ikejima, T.; Li, L.-H.; Guo, C. Med. Chem.
Res. 2013, 22, 3170. (b) Li, H.-Q.; Lv, P.-C.; Yan, T.; Zhu, H.-L.
Anticancer Agents Med. Chem. 2009, 9, 471. (c) Cainap, C.; Qin,
S.; Huang, W.-T.; Chung, I. J.; Pan, H.; Cheng, Y.; Kudo, M.; Kang,
Y.-K.; Chen, P.-J.; Toh, H.-C.; Gorbunova, V.; Eskens, F.; Qian, J.;
McKee, M. D.; Ricker, J. L.; Carlson, D. M.; El-Nowiem, S. J. Clin.
Oncol. 2015, 33, 172. (d) Motzer, R. J.; Nosov, D.; Eisen, T.;
Bondarenko, I.; Lesovoy, V.; Lipatov, O.; Tomczak, P.; Lyulko, O.;
Alyasova, A.; Harza, M.; Kogan, M.; Alekseev, B.; Sternberg, C.;
Szczylik, C.; Cella, D.; Ivanescu, C.; Krivoshib, A.; Strahs, A.;
Esteves, B.; Berkenblity, A.; Hutson, T. E. J. Clin. Oncol. 2013, 31,
3791.
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Gaudreault, R. Eur. J. Med. Chem. 2010, 45, 2928. (b) Fortin, J.;
Lacroix, J.; Desjardins, M.; Patenaude, A.; Petitclerc, E.;
Gaudreault, R. Bioorg. Med. Chem. 2007, 15, 4456. (c) Mounetou,
E.; Miot-Noirault, E.; Gaudreault, R.; Madelmont, J. C. Invest.
New Drugs 2010, 28, 124. (d) Trzeciakiewicz, A.; Fortin, S.;
Moreau, E.; Gaudreault, R.; Lacroix, J.; Chambon, C.; Communal,
Y.; Chezal, J.-M.; Miot-Noirault, E.; Bouchon, B.; Degoul, F. Bio-
chem. Pharmacol. 2011, 81, 1116.
N-(4-Iodophenyl)-N′-(pyridin-2-yl)urea (2m)
Brown powder; yield: 69 mg (81%); mp 200 (dec.); Rf = 0.38 (EtOAc/
hexane, 1:1).
IR (KBr): 3368, 3214, 3112, 3083, 3055, 2977, 2916, 1697, 1600, 1581,
1550, 1509, 1478, 1418, 1395, 1319, 1151, 999, 849, 817, 775, 731,
521, 503 cm–1
.
1H NMR (500 MHz, DMSO-d6): δ = 10.62 (s, 1 H), 9.49 (s, 1 H), 8.29–
8.26 (m, 1 H), 7.77–7.72 (m, 1 H), 7.63 (d, J = 8.7 Hz, 2 H), 7.47 (d, J =
8.4 Hz, 1 H), 7.38 (d, J = 8.7 Hz, 2 H), 7.03–6.99 (m, 1 H).
13C NMR (125 MHz, DMSO-d6): δ = 152.7, 152.0, 146.9, 138.9, 138.6,
137.4, 121.0, 117.6, 111.9, 85.5.
HRMS (ESI): m/z [M + H]+ calcd for C12H11N3OI: 339.9941; found:
339.9945.
Acknowledgment
The authors would like to thank CNPq and FAPERJ for financial sup-
port. C.M.S. thanks CAPES, M.T.C. thanks PIBIC/UFRJ and M.C.S.M.
thanks CNPq for fellowships.
(10) Viana, G. M.; Aguiar, L. C. S.; Ferrão, J.; Simas, A. B. C.;
Vasconcelos, M. G. Tetrahedron Lett. 2013, 54, 936.
(11) Senra, J. D.; Viana, G. M.; Malta, L. F.; Simas, A. B. C.; Aguiar, L. C.
S. ChemCatChem 2016, 8, 192.
Supporting Information
(12) (a) Zhan, Y.; Zhang, H.; Li, J.; Zhang, Y.; Zhang, J.; He, L. J. Cell.
Mol. Med. 2015, 19, 1614. (b) Wang, C.; Dong, J.; Zhang, Y.;
Wang, F.; Gao, H.; Li, P.; Wang, S.; Zhang, J. Med. Chem. Commun.
2013, 4, 1434.
Supporting information for this article is available online at
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–G