BULLETIN OF THE
Article
Synthesis of Tetrasubstituted Thieno[3,2-b]pyridin-5(4H)-one
KOREAN CHEMICAL SOCIETY
Chem. Abstr. 1986, 105, 60612; (b) F. Suzuki, Y. Miwa,
H. Hayashi, T. Kuroda, K. Ohmori, H. Nakajima, European
Patent 505058, Chem. Abstr. 1992, 117, 251343;
(c) F. Suzuki, Y. Miwa, H. Hayashi, A. Ishii, S. Ichikawa,
I. Miki, European Patent 503844, Chem. Abstr. 1993, 118,
59697; (d) J. R. Allen, R. Burli, M. J. Frohn, R. W. Hungate,
S. C. Neira, A. B. Reed, PCT Patent 137060, Chem. Abstr.
2008, 149, 556941; (e) X. Huang, A. Palani, R. G. Aslanian,
PCT Patent 060036, Chem. Abstr. 2011, 154, 580318.
8. M. Zhang, J. Tamiya, L. Nguyen, M. W. Rowbottom,
B. Dyck, T. D. Vickers, J. Grey, D. A. Schwarz, C. E. Heise,
J. Haelewyn, M. S. Mistry, V. S. Goodfellow, Bioorg. Med.
Chem. Lett. 2007, 17, 2535.
model SMM consisting of small organic molecules with and
without previously known protein partners, including the
tagged compounds described in this report.
Acknowledgments. Financial support from Korea Research
Institute of Chemical Technology is gratefully acknowledged.
References
1. M.-K. Jeon, M.-K. Kang, K. H. Park, Tetrahedron 2012,
68, 6038.
2. For some recent review/original articles including descriptions
on the SMMs, see: (a) M. M. Kemp, M. Weïwer,
A. N. Koehler, Bioorg. Med. Chem. 2012, 20, 1979;
(b) Y. M. Foong, J. Fu, S. Q. Yao, M. Uttamchandani, Curr.
Opin. Chem. Biol. 2012, 16, 234; (c) D. E. Casalena,
D. Wassaf, A. N. Koehler, In Chemical Proteomics: Methods
and Protocols, G. Drewes, M. Bantscheff Eds., Humana Press,
New York, 2012, p. 249; (d) H. Sun, G. Y. J. Chen, S. Q. Yao,
Chem. Biol. 2013, 20, 685; (e) H. Sun, In Diversity-Oriented
Synthesis, A. Trabocchi Ed., John Wiley & Sons, Inc., New Jer-
sey, 2013, p. 431; (f ) J. A. Hong, D. V. Neel, D. Wassaf,
F. Caballero, A. N. Koehler, Curr. Opin. Chem. Biol. 2014, 18,
21; (g) V. Sakanyan, M. Angelini, M. Le Béchec,
M. F. Lecocq, F. Benaiteau, B. Rousseau, A. Gyulkhandanyan,
L. Gyulkhandanyan, C. Logé, E. Reiter, C. Roussakis,
3. (a) N. Kanoh, A. Asami, M. Kawatani, K. Honda, S. Kumashiro,
H. Takayama, S. Simizu, T. Amemiya, Y. Kondoh,
S. Hatakeyama, K. Tsuganezawa, R. Utata, A. Tanaka,
S. Yokoyama, H. Tashiro, H. Osada, Chem. Asian J. 2006, 1,
789; (b) N. Kanoh, M. Kyo, K. Inamori, A. Ando, A. Asami,
A. Nakao, H. Osada, Anal. Chem. 2006, 78, 2226;
(c) M. Kurosu, W. A. Mowers, Bioorg. Med. Chem. Lett. 2006,
16, 3392; (d) M. Valles-Miret, M. Bradley, Tetrahedron Lett.
2011, 52, 6819.
9. See Supporting Information for the details of preparative pro-
cedures and/or characterization data.
10. For the related example of synthetic method for the 3-amino-
5-arylthiophene-2-carboxylate, see: X. Bu, Chinese Patent
10505613, Chem. Abstr. 2011, 154, 259387.
11. For other synthetic methods for 3-amino-5-arylthiophene-2-
carboxylates, see: (a) I. Abdillahi, G. Kirsch, Synthesis 2010,
1428; (b) M. Murai, R. Hatano, S. Kitabata, K. Ohe, Chem.
Commun. 2011, 47, 2375; (c) F. Derridj, K. S. Larbi,
J. Roger, S. Djebbar, H. Doucet, Tetrahedron 2012, 68, 7463.
12. For recent examples of Mitsunobu reaction of trifluoroaceta-
mides, see: (a) R. A. Turner, N. E. Hauksson, J. H. Gipe,
R. S. Lokey, Org. Lett. 2013, 15, 5012; (b) R. Kakuchi,
P. Theato, Macromol. Rapid Commun. 2014, 35, 661.
13. For the related example of Mitsunobu reaction for N-
trifluoroacetamide of 3-aminothiophene-2-carboxylate, see:
B. Simoneau, P. Deroy, L. Fader, A.-M. Faucher, A. Gagnon,
C. Grand-Maitre, S. Kawai, S. Landry, J.-F. Mercier, J. Rancourt,
PCT Patent 100838, Chem. Abstr. 2011, 155, 352580.
14. For the related example of the reaction conditions, see: M.-
K. Jeon, M.-S. Kim, J.-J. Kwon, Y.-D. Gong, D.-H. Lee, Tet-
rahedron 2008, 64, 9060.
15. B. K. Albrecht, J. E. Audia, A. Cook, A. Gagnon, J.-
C. Harmange, C. G. Naveschuk, PCT Patent 075083, Chem.
Abstr. 2013, 159, 9102.
4. For a review article, see: W. Zhang, D. P. Curran, Tetrahe-
dron 2006, 62, 11837.
16. F. X. Tavares, K. A. Al-Barazanji, E. C. Bigham,
M. J. Bishop, C. S. Britt, D. L. Carlton, P. L. Feldman,
A. S. Goetz, M. K. Grizzle, Y. C. Guo, A. L. Handlon,
D. L. Hertzog, D. M. Ignar, D. G. Lang, R. J. Ott, A. J. Peat,
H.-Q. Zhou, J. Med. Chem. 2006, 49, 7095.
17. Formation of alkyl 2,2,2-trifluoroacetimidates from O-
alkylation as minor products was detected on analytical TLC.
However, purification of the minor products by silica gel col-
umn chromatography failed, maybe because of instability on
silica gel.
18. In the cases of ethyl mesylate and isopropyl mesylate,
β-elimination of the reagents under basic reaction conditions
may be dominant factor in the failure of the reactions. In fact,
the use of 4-(t-butoxycarbonyl)phenethyl mesylate as alkylation
agent gave 4-(t-butoxycarbonyl)styrene as a main side product.
19. V. S. Korotkov, A. Ludwig, O. V. Larionov, A. V. Lygin,
M. Grollc, A. de Meijere, Org. Biomol. Chem. 2011, 9, 7791.
20. J. Close, J. Grimm, R. W. Heidebrecht Jr., S. Kattar,
T. A. Miller, K. M. Otte, S. Peterson, P. Siliphaivanh,
P. Tempest, K. J. Wilson, D. J. Witter, PCT Patent 010985,
Chem. Abstr. 2008, 148, 192076.
5. For the concept of drug-likeness, see: G. R. Bickerton,
G. V. Paolini, J. Besnard, S. Muresan, A. L. Hopkins, Nat.
Chem. 2012, 4, 90 and references cited therein.
6. For some articles on the related thienopyridinone derivatives,
see: (a) J. R. Bantick, H. G. Beaton, S. L. Cooper, S. Hill,
S. C. Hirst, T. McInally, J. Spencer, A. C. Tinker,
P. A. Willis, Bioorg. Med. Chem. Lett. 1994, 4, 127; (b) H.-
P. Buchstaller, C. D. Siebert, R. Steinmetz, I. Frank,
M. L. Berger, R. Gottschlich, J. Leibrock, M. Krug,
D. Steinhilber, C. R. Noe, J. Med. Chem. 2006, 49, 864;
(c) G. Zhao, R. R. Iyengar, A. S. Judd, B. Cool, W. Chiou,
L. Kifle, E. Frevert, H. Sham, P. R. Kym, Bioorg. Med.
Chem. Lett. 2007, 17, 3254; (d) A. H. Mermerian, A. Case,
R. L. Stein, G. D. Cuny, Bioorg. Med. Chem. Lett. 2007, 17,
3729; (e) R. Tedesco, D. Chai, M. G. Darcy, D. Dhanak,
D. M. Fitch, A. Gates, V. K. Johnston, R. M. Keenan,
J. Lin-Goerke, R. T. Sarisky, A. N. Shaw, K. L. Valko,
K. J. Wiggall, M. N. Zimmerman, K. J. Duffy, Bioorg. Med.
Chem. Lett. 2009, 19, 4354.
7. For the biological activities of thieno[3,2-b]pyridin-5(4H)-one
derivatives, see: (a) T. L. Wright, European Patent 177924,
Bull. Korean Chem. Soc. 2016
© 2016 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
7