6976
E. Uh et al. / Bioorg. Med. Chem. Lett. 21 (2011) 6973–6976
27. Reichenberg, A.; Wiesner, J.; Weidemeyer, C.; Dreiseidler, E.; Sanderbrand, S.;
Acknowledgments
Altincicek, B.; Beck, E.; Schlitzer, M.; Jomaa, H. Bioorg. Med. Chem. Lett. 2001, 11,
833.
This work was supported by funding from the GWU Depart-
ment of Chemistry, the GWU University Facilitating Fund, the
Intramural Research Program of the NIAID (NIH), the American
Lebanese Syrian Associated Charities (ALSAC), and NIH (AI086453
to C.S.D.).
28. Schluter, K.; Walter, R. D.; Bergmann, B.; Kurz, T. Eur. J. Med. Chem. 2006, 41,
1385.
29. Schultz, C. Bioorg. Med. Chem. 2003, 11, 885.
30. Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Arch. Pharm. (Weinheim) 2007,
340, 667.
31. Andaloussi, M.; Henriksson, L. M.; Wieckowska, A.; Lindh, M.; Bjorkelid, C.;
Larsson, A. M.; Suresh, S.; Iyer, H.; Srinivasa, B. R.; Bergfors, T.; Unge, T.;
Mowbray, S. L.; Larhed, M.; Jones, T. A.; Karlen, A. J. Med. Chem. 2011, 54,
4964.
References and notes
32. Deng, L.; Diao, J.; Chen, P.; Pujari, V.; Yao, Y.; Cheng, G.; Crick, D. C.; Prasad, B.
V.; Song, Y. J. Med. Chem. 2011, 54, 4721.
33. Kojo, H.; Shigi, Y.; Nishida, M. J. Antibiot. 1980, 33, 44.
34. Okuhara, M.; Kuroda, Y.; Goto, T.; Okamoto, M.; Terano, H.; Kohsaka, M.; Aoki,
H.; Imanaka, H. J. Antibiot. (Tokyo) 1980, 33, 13.
35. Brown, A. C.; Parish, T. BMC Microbiol. 2008, 8, 78.
36. Dhiman, R. K.; Schaeffer, M. L.; Bailey, A. M.; Testa, C. A.; Scherman, H.; Crick, D.
C. J. Bacteriol. 2005, 187, 8395.
1. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev. Drug Disc.
2007, 6, 29.
2. Silver, L. L. Clin. Microbiol. Rev. 2011, 24, 71.
5. Eoh, H.; Brennan, P. J.; Crick, D. C. Tuberculosis (Edinb) 2008.
6. Proteau, P. J. Bioorg. Chem. 2004, 32, 483.
7. Rohdich, F.; Bacher, A.; Eisenreich, W. Bioorg. Chem. 2004, 32, 292.
8. Rohdich, F.; Bacher, A.; Eisenreich, W. Biochem. Soc. Trans. 2005, 33, 785.
9. Singh, N.; Cheve, G.; Avery, M. A.; McCurdy, C. R. Curr. Pharm. Des. 2007, 13, 1161.
10. Testa, C. A.; Brown, M. J. Curr. Pharm. Biotechnol. 2003, 4, 248.
11. Henriksson, L. M.; Unge, T.; Carlsson, J.; Aqvist, J.; Mowbray, S. L.; Jones, T. A. J.
Biol. Chem. 2007, 282, 19905.
12. Mac Sweeney, A.; Lange, R.; Fernandes, R. P.; Schulz, H.; Dale, G. E.;
Douangamath, A.; Proteau, P. J.; Oefner, C. J. Mol. Biol. 2005, 345, 115.
13. Devreux, V.; Wiesner, J.; Goeman, J. L.; Van der Eycken, J.; Jomaa, H.; Van
Calenbergh, S. J. Med. Chem. 2006, 49, 2656.
37. Sakamoto, Y.; Furukawa, S.; Ogihara, H.; Yamasaki, M. Biosci., Biotechnol.,
Biochem. 2003, 67, 2030.
38. Zwierzak, A.; Osowska, K. Synthesis 1984, 223.
39. Blazewska, K.; Gajda, T. Tetrahedron 2003, 59, 10249.
40. Haemers, T.; Wiesner, J.; Giessmann, D.; Verbrugghen, T.; Hillaert, U.; Ortmann,
R.; Jomaa, H.; Link, A.; Schlitzer, M.; Van Calenbergh, S. Bioorg. Med. Chem.
2008, 16, 3361.
41. Villemin, D.; Simeon, F.; Decreus, H.; Jaffres, P.-A. Phosphorus, Sulfur Silicon
1998, 133, 209.
42. Fokin, A. A.; Yurchenko, A. G.; Rodionov, V. N.; Gunchenko, P. A.; Yurchenko, R.
I.; Reichenberg, A.; Wiesner, J.; Hintz, M.; Jomaa, H.; Schreiner, P. R. Org. Lett.
2007, 9, 4379.
14. Devreux, V.; Wiesner, J.; Jomaa, H.; Rozenski, J.; Van der Eycken, J.; Van
Calenbergh, S. J. Org. Chem. 2007, 72, 3783.
15. Devreux, V.; Wiesner, J.; Jomaa, H.; Van der Eycken, J.; Van Calenbergh, S.
Bioorg. Med. Chem. Lett. 2007, 17, 4920.
16. Haemers, T.; Wiesner, J.; Busson, R.; Jomaa, H.; Van Calenbergh, S. Eur. J. Org.
Chem. 2006, 3856.
17. Haemers, T.; Wiesner, J.; Van Poecke, S.; Goeman, J.; Henschker, D.; Beck, E.;
Jomaa, H.; Van Calenbergh, S. Bioorg. Med. Chem. Lett. 2006, 16, 1888.
18. Jomaa, H.; Wiesner, J.; Sanderbrand, S.; Altincicek, B.; Weidemeyer, C.; Hintz,
M.; Turbachova, I.; Eberl, M.; Zeidler, J.; Lichtenthaler, H. K.; Soldati, D.; Beck, E.
Science 1999, 285, 1573.
19. Kuntz, L.; Tritsch, D.; Grosdemange-Billiard, C.; Hemmerlin, A.; Willem, A.;
Bach, T. J.; Rohmer, M. Biochem. J. 2005, 386, 127.
20. Kurz, T.; Behrendt, C.; Kaula, U.; Bergmann, B.; Walter, R. D. Aust. J. Chem. 2007,
60, 154.
21. Kurz, T.; Behrendt, C.; Pein, M.; Kaula, U.; Bergmann, B.; Walter, R. D. Arch.
Pharm. (Weinheim) 2007, 340, 661.
22. Kurz, T.; Schluter, K.; Kaula, U.; Bergmann, B.; Walter, R. D.; Geffken, D. Bioorg.
Med. Chem. 2006, 14, 5121.
43. Ohler, E.; Kanzler, S. Synthesis 1995, 539.
44. Compound 21. A solution of compound 20a (0.29 g, 0.63 mmol) in dry EtOH
(50 mL) was hydrogenated over 10% Pd/C (112.3 mg) overnight. After filtration
and evaporation, the crude product was purified by column chromatography
using ethyl acetate to give 0.18 g (0.48 mmol, 76%) of the desired product as a
light yellow viscous oil. 1H NMR (CDCl3, 200 MHz), d (ppm): 0.90 (t, 6H); 1.22–
1.50 (m, 12H); 1.57–2.12 (m, 8H); 2.17 (s, 3H); 3.76 (t, 2H); 3.98 (q, 4H). ESI-MS
m/z 366 ([M+H]+), 388 ([M+Na]+).
45. Compound 23. Prepared from 20c in 65% yield as described above. 1H NMR
(CDCl3, 200 MHz), d (ppm): 1.49 (s, 18H); 1.99–2.13 (m, 4H); 2.17 (s, 3H); 3.77
(t, 2H); 4.51 (d, 4H); 8.93 (br s, 1H). ESI-MS m/z 426 ([M+H]+).
46. Compound 25. Prepared from 20e in 43% yield as described above. 1H NMR
(CDCl3, 200 MHz), d (ppm): 1.50 (s, 18H); 1.58 (d, 6H); 1.73–1.94 (m, 4H); 1.98
(s, 3H); 3.33 (q, 2H); 6.27–6.42 (m, 2H). ESI-MS m/z 470 ([MÀCH3]+).
47. Compound 26. Prepared from 20f in 59% yield as described above. 1H NMR
(CDCl3, 200 MHz), d (ppm): 1.85–2.10 (m, 4H); 2.15 (s, 3H); 3.62–3.77 (m, 2H);
5.88 (s, 2H); 5.94 (s, 2H); 7.40–7.67 (m, 6H); 7.98–8.20 (m, 4H). ESI-MS m/z 466
([M+H]+).
23. Kurz, T.; Schluter, K.; Pein, M.; Behrendt, C.; Bergmann, B.; Walter, R. D. Arch.
Pharm. (Weinheim) 2007, 340, 339.
24. Ortmann, R.; Wiesner, J.; Reichenberg, A.; Henschker, D.; Beck, E.; Jomaa, H.;
Schlitzer, M. Bioorg. Med. Chem. Lett. 2003, 13, 2163.
48. Kim, P.; Zhang, L.; Manjunatha, U. H.; Singh, R.; Patel, S.; Jiricek, J.; Keller, T.
H.; Boshoff, H. I.; Barry, C. E., 3rd; Dowd, C. S. J. Med. Chem. 2009, 52,
1317.
25. Ortmann, R.; Wiesner, J.; Reichenberg, A.; Henschker, D.; Beck, E.; Jomaa, H.;
Schlitzer, M. Arch. Pharm. (Weinheim) 2005, 338, 305.
49. Yendapally, R.; Hurdle, J. G.; Carson, E. I.; Lee, R. B.; Lee, R. E. J. Med. Chem. 2008,
51, 1487.
26. Ortmann, R.; Wiesner, J.; Silber, K.; Klebe, G.; Jomaa, H.; Schlitzer, M. Arch.
Pharm. (Weinheim) 2007, 340, 483.
50. McKenney, E. S.; Sargent, M.; Khan, H.; Couch, R. D.; Uh, E.; Jackson, E. R.; San
Jose, G.; Dowd, C. S.; Van Hoek, M. L., submitted for publication.