Organic Letters
Letter
O. Synthesis 2009, 4087. (n) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem.
Res. 2008, 41, 222.
(2) For reviews, see: (a) De Sarkar, S.; Liu, W.; Kozhushkov, S. I.;
Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461. (b) Mo, F.; Tabor, J.
R.; Dong, G. Chem. Lett. 2014, 43, 264. (c) Engle, K. M.; Mei, T.-S.;
Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788.
Table 3. Chemical Structures and IC50 Values of Aurora A
Inhibitors
(3) For the seminal reports on this area, see: (a) Zhang, Y.-H.; Yu, J.-Q.
J. Am. Chem. Soc. 2009, 131, 14654. (b) Chen, X.; Hao, X.-S.; Goodhue,
C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790. (c) Desai, L. V.; Malik,
H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
(4) Recent review on C−H oxygenation by Ru catalysis:
Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem.
Commun. 2014, 50, 29.
(5) (a) Yang, Y.; Rao, Y. Org. Lett. 2012, 14, 2874. (b) Thirunavukkar-
asu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14, 4210. For the
C−H oxygenation on aryl Weinreb amides, see: (c) Yang, F.;
Ackermann, L. Org. Lett. 2013, 15, 718.
(6) (a) Shan, G.; Yang, X.; Ma, L.; Rao, Y. Angew. Chem., Int. Ed. 2012,
51, 13070. (b) Mo, F.; Trzepkowski, L. J.; Dong, G. Angew. Chem., Int.
Ed. 2012, 51, 13075. (c) Choy, P. Y.; Kwong, F. Y. Org. Lett. 2013, 15,
270.
(7) Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett.
2012, 14, 6206.
(8) (a) Kang, D.; Hong, S. Org. Lett. 2015, 17, 1938. (b) Shin, Y.; Yoo,
C.; Moon, Y.; Lee, Y.; Hong, S. Chem.Asian J. 2015, 10, 878. (c) Kim,
Y.; Moon, Y.; Kang, D.; Hong, S. Org. Biomol. Chem. 2014, 12, 3413.
(d) Moon, Y.; Kim, Y.; Hong, H.; Hong, S. Chem. Commun. 2013, 49,
8323. (e) Kim, D.; Min, M.; Hong, S. Chem. Commun. 2013, 49, 4021.
(f) Min, M.; Kim, Y.; Hong, S. Chem. Commun. 2013, 49, 196. (g) Moon,
Y.; Kwon, D.; Hong, S. Angew. Chem., Int. Ed. 2012, 124, 11495.
(h) Moon, Y.; Hong, S. Chem. Commun. 2012, 48, 7191. (i) Min, M.;
Choe, H.; Hong, S. Asian J. Org. Chem. 2012, 1, 47. (j) Kim, D.; Hong, S.
Org. Lett. 2011, 13, 4466.
should be considered in the design of potent aurora kinase
inhibitors.
ASSOCIATED CONTENT
■
S
* Supporting Information
(9) (a) Salmela, A.-L.; Pouwels, J.; Kukkonen-Macchi, A.; Waris, S.;
Experimental procedure and characterization of new compounds
(1H and 13C NMR spectra). The Supporting Information is
Toivonen, P.; Jaakkola, K.; Maki-Jouppila, J.; Kallio, L.; Kallio, M. K.
̈
Exp. Cell Res. 2012, 318, 578. (b) Xie, F.; Lang, Q.; Zhou, M.; Zhang, H.;
Zhang, Z.; Zhang, Y.; Wan, B.; Huang, Q.; Yu, L. Eur. J. Pharm. Sci. 2012,
46, 388.
(10) For selected reviews, see: (a) Lens, S. M. A.; Voest, E. E.;
Medema, R. H. Nat. Rev. Cancer 2010, 10, 825. (b) Keen, N.; Taylor, S.
Nat. Rev. Cancer 2004, 4, 927.
AUTHOR INFORMATION
Corresponding Author
■
(11) Bayliss, R.; Sardon, T.; Vernos, I.; Conti, E. Mol. Cell 2003, 12,
851.
Author Contributions
§K.K. and H.C. contributed equally.
Notes
(12) Discovery Studio software was used for docking simulation for
Aurora binding modes.
(13) For the hypervalent iodine-mediated C-3 hydroxylation of
chromones and flavones, see: Moriarty, R. M.; Prakash, O. J. Heterocycl.
Chem. 1985, 22, 583.
The authors declare no competing financial interest.
(14) (a) Lo, V. K.-Y.; Guo, Z.; Choi, M. K.-W.; Yu, W.-Y.; Huang, J.-S.;
Che, C.-M. J. Am. Chem. Soc. 2012, 134, 7588. (b) Tocher, D. A.; Gould,
R. O.; Stephenson, T. A.; Bennett, M. A.; Ennett, J. P.; Matheson, T. W.;
Sawyer, L.; Shah, V. K. J. Chem. Soc., Dalton Trans. 1983, 1571.
(15) (a) Schinkel, M.; Wallbaum, J.; Kozhushkov, S. I.; Marek, I.;
Ackermann, L. Org. Lett. 2013, 15, 4482. (b) Kumar, N. Y. P.;
Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145. (c) Diers,
E.; Kumar, N. Y. P.; Mejuch, T.; Marek, I.; Ackermann, L. Tetrahedron
2013, 69, 4445. (d) Ackermann, L.; Pospech, J.; Potukuchi, H. K. Org.
Lett. 2012, 14, 2146. (e) Ackermann, L.; Vincente, R.; Potukuchi, H. K.;
Pirovano, V. Org. Lett. 2010, 12, 5032.
(16) (a) Shang, M.; Zeng, S.-H.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. Org.
Lett. 2013, 15, 5286. (b) Ackermann, L.; Vincent, R.; Potukuchi, H. K.;
Pirovano, V. Org. Lett. 2010, 12, 5032. (c) Flegeau, E. F.; Bruneau, C.;
Dixneuf, P. H.; Jutand, A. J. J. Am. Chem. Soc. 2011, 133, 10161.
(17) IC50 determinations were performed at Reaction Biology Corp.
(18) Luteolin derivatives were synthesized via Suzuki cross-coupling
from 3m or 3y.
ACKNOWLEDGMENTS
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This research was supported financially by the Institute for Basic
Science (IBS-R010-G1) and National Research Foundation of
Korea (NRF) funded by the Ministry of Education, Science and
Technology (NRF-2010-0022179).
REFERENCES
■
(1) For selected recent reviews, see: (a) Ackermann, L. Acc. Chem. Res.
2014, 47, 281. (b) Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927.
(c) Mousseau, J. J.; Charrette, A. B. Acc. Chem. Res. 2013, 46, 412.
(d) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112,
5879. (e) Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Tetrahedron 2012, 68, 5130.
(f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40,
5068. (g) Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc.
̈
Rev. 2011, 40, 4740. (h) Ackerman, L. Chem. Rev. 2011, 111, 1315.
(i) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. (j) Sun, C.-L.;
Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. (k) Lyons, T. W.; Sanford,
M. S. Chem. Rev. 2010, 110, 1147. (l) Colby, D. A.; Bergman, R. G.;
Ellman, J. A. Chem. Rev. 2010, 110, 624. (m) Kulkarni, A. A.; Daugulis,
D
Org. Lett. XXXX, XXX, XXX−XXX