Beilstein J. Org. Chem. 2018, 14, 2529–2536.
3. Fader, L. D.; Malenfant, E.; Parisien, M.; Carson, R.; Bilodeau, F.;
Landry, S.; Pesant, M.; Brochu, C.; Morin, S.; Chabot, C.; Halmos, T.;
Bousquet, Y.; Bailey, M. D.; Kawai, S. H.; Coulombe, R.; LaPlante, S.;
Jakalian, A.; Bhardwaj, P. K.; Wernic, D.; Schroeder, P.; Amad, M.;
Edwards, P.; Garneau, M.; Duan, J.; Cordingley, M.; Bethell, R.;
Mason, S. W.; Bös, M.; Bonneau, P.; Poupart, M.-A.; Faucher, A.-M.;
Simoneau, B.; Fenwick, C.; Yoakim, C.; Tsantrizos, Y.
4. Fenwick, C.; Amad, M.; Bailey, M. D.; Bethell, R.; Bös, M.;
Bonneau, P.; Cordingley, M.; Coulombe, R.; Duan, J.; Edwards, P.;
Fader, L. D.; Faucher, A.-M.; Garneau, M.; Jakalian, A.; Kawai, S.;
Lamorte, L.; LaPlante, S.; Luo, L.; Mason, S.; Poupart, M.-A.;
Rioux, N.; Schroeder, P.; Simoneau, B.; Tremblay, S.; Tsantrizos, Y.;
Witvrouw, M.; Yoakim, C. Antimicrob. Agents Chemother. 2014, 58,
(t, J = 7.1 Hz, 1H, Cm-H); 13C NMR (DMSO-d6, 100 MHz)
δ 172.0 (s, Ca), 166.4 (s, Cb), 149.4 (s, Cc), 138.0 (s, Cd),
134.9 (d, Ce), 127.1 (d, Cf), 126.0 (s, Cg), 120.6 (d, Ch), 116.3
(s, Ci), 115.0 (s, Cj), 60.4 (t, Ck), 18.2 (q, Cl), 14.1 (q, Cm);
HRMS (ESI): calcd for [C13H12BrNO3 + Na]+ 331.989277;
found: 331.988788; anal. calcd for C13H12BrNO3: C, 39.70; H,
1.67; found C, 39.51; H, 1.74.
Supporting Information
Supporting Information File 1
Experimental procedures and analytical data.
5. Kessl, J. J.; Jena, N.; Koh, Y.; Taskent-Sezgin, H.; Slaughter, A.;
Feng, L.; de Silva, S.; Wu, L.; Le Grice, S. F. J.; Engelman, A.;
Fuchs, J. R.; Kvaratskhelia, M. J. Biol. Chem. 2012, 287,
Supporting Information File 2
IR, NMR and mass spectra, as well as elemental analyses.
6. Feng, L.; Sharma, A.; Slaughter, A.; Jena, N.; Koh, Y.; Shkriabai, N.;
Larue, R. C.; Patel, P. A.; Mitsuya, H.; Kessl, J. J.; Engelman, A.;
Fuchs, J. R.; Kvaratskhelia, M. J. Biol. Chem. 2013, 288,
7. Di Santo, R. J. Med. Chem. 2014, 57, 539–566.
Acknowledgements
8. Quashie, P. K.; Sloan, R. D.; Wainberg, M. A. BMC Med. 2012, 10, 34.
JK thanks the National Institute of Allergy and Infectious
Disease for AI127282. Funding for the Bruker UltraShield Plus
400 MHz NMR and ThermoFinnigan LXQ ESI LC–MS used in
this research was provided by National Science Foundation
Major Research Instrumentation under Grant Numbers 0840390
and 0639208, respectively. NGJ, JDH, and EBC thank the USM
INTERFACE National Science Foundation National Research
Trainee under Grant Number 1449999. We thank the Univer-
sity of Southern Mississippi Office of the Vice President for
Research for financial support, laboratory space and facilities.
MGD is a 2015 and 2018 recipient of the Lucas Award for
Faculty Excellence sponsored by the USM Office of the
Provost.
9. Ingale, K. B.; Bhatia, M. S. Antiviral Chem. Chemother. 2011, 22,
10.Christ, F.; Voet, A.; Marchand, A.; Nicolet, S.; Desimmie, B. A.;
Marchand, D.; Bardiot, D.; Van der Veken, N. J.; Van Remoortel, B.;
Strelkov, S. V.; De Maeyer, M.; Chaltin, P.; Debyser, Z.
11.Fandrick, K. R.; Li, W.; Zhang, Y.; Tang, W.; Gao, J.; Rodriguez, S.;
Patel, N. D.; Reeves, D. C.; Wu, J.-P.; Sanyal, S.; Gonnella, N.; Qu, B.;
Haddad, N.; Lorenz, J. C.; Sidhu, K.; Wang, J.; Ma, S.; Grinberg, N.;
Lee, H.; Tsantrizos, Y.; Poupart, M.-A.; Busacca, C. A.; Yee, N. K.;
Lu, B. Z.; Senanyake, C. H. Angew. Chem., Int. Ed. 2015, 54,
12.Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron
13.Kessl, J. J.; Sharma, A.; Kvaratskhelia, M.
Methods Mol. Biol. (N. Y., NY, U. S.) 2016, 1354, 149–164.
ORCID® iDs
14.Chattha, F. A.; Munawar, M. A.; Ashraf, M.; Nagra, S. A.;
Mehr-Un-Nisa; Fatima, I. J. Chil. Chem. Soc. 2012, 57, 1237–1239.
15.Avetisyan, A. A.; Aleksanyana, I. L.; Pivazyan, A. A.
Russ. J. Org. Chem. 2004, 40, 889–891.
16.Kappe, T.; Stadlbauer, W. Isatoic Anhydrides and Their Uses in
Heterocyclic Synthesis in Advances in Heterocyclic Chemistry;
Academic Press, 1981; Vol. 28, pp 127–182.
18.Coppola, G. M.; Hardtmann, G. E. J. Heterocycl. Chem. 1979, 16,
References
1. Chung, P.-Y.; Bian, Z.-X.; Pun, H.-Y.; Chan, D.; Chan, A. S.-C.;
Chui, C.-H.; Tang, J. C.-O.; Lam, K.-H. Future Med. Chem. 2015, 7,
19.Mai, A.; Rotili, D.; Tarantino, D.; Ornaghi, P.; Tosi, F.; Vicidomini, C.;
Sbardella, G.; Nebbioso, A.; Miceli, M.; Altucci, L.; Filetici, P.
2. Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57,
2535