5818
S. J. Kim et al. / Bioorg. Med. Chem. Lett. 18 (2008) 5815–5818
7. Griera, R.; Llopart, C. C.; Amat, M.; Bosch, J.; Castilo, J. C. D.; Huguet, J. Bioorg.
Acknowledgments
Med. Chem. Lett. 2005, 15, 2515.
8. Wilson, P.; Andrews, J. A.; Charlesworth, R.; Walesby, R.; Singer, M.; Farrell, D.
J.; Robbins, M. J. Antimicrob. Chemother. 2003, 51, 186.
We thank Hawon Pharmaceuticals Co. which supported us with
fund and also Mrs. Sun Hee Seo for performing the antibacterial
tests.
9. Iso, Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot. 1996, 49, 199.
10. Jeon, H.; Jo, Nam.; Cho, J.; Oh, C.-H. Eur. J. Med. Chem. 2007, 42, 358.
11. Kim, S.; Park, B.; Jo, Nam.; Cho, J.; Oh, C.-H. Eur. J. Med. Chem. 2007, 42, 1176.
12. Compound 9g: 1H NMR (CDCl3): d 1.97 (s, 9H), 3.96 (s, 4H), 7.12 (t, 1H,
J = 7.0 Hz), 7.97–8.04 (m, 2H). HRMS(FAB) Calcd for C8H8FN3O4S 261.0220.
Found 261.0221.
References and notes
Compound 11g: 1H NMR (CDCl3):
d 1.53 (s, 9H), 3.78 (t, 2H, J = 3.3 Hz),
1. Service, R. F. Science 1995, 270, 724.
3.97 (t, 2H, J = 3.1 Hz), 5.18 (s, 2H), 7.00 (d, 1H, J = 3.3 Hz), 7.29–7.51 (m,
2. Swartz, M. N. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2420.
3. Tomasz, A. N. Engl. J. Med. 1994, 330, 1247.
8H). HRMS(FAB) Calcd for C16H16FN3O4S 365.0846. Found 365.0849.
Compound 12g: 1H NMR (CDCl3):
d 3.72 (t, 2H, J = 3.5 Hz), 3.91 (t, 2H,
4. For a comprehensive list of references for this area, see: (a) Selvakumar, N.;
Srinivas, D.; Khera, M. K.; Kumar, M. S.; Srinivas, D.; Kumar, M. S.; Mamidi, N. V.
S. R.; Sarnaik, H.; Chandrasekar, C.; Rao, B. S.; Raheem, M. A.; Das, J.; Iqbal, J.;
Rahagopalan, R. J. Med. Chem. 2002, 45, 3953; (b) Selvakumar, N.; Reddy, B. Y.;
Kumar, G. S.; Khera, M. K.; Srinivas, D.; Kumar, M. S.; Das, J.; Iqbal, J.; Trehan, J.;
Trehan, S. Bioorg. Med. Chem. Lett. 2006, 16, 4416.
J = 3.6 Hz), 4.10–4.17 (m, 6H),4.70–4.74 (m, 1H), 7.21 (d, 1H, J = 4.3 Hz),
7.26–7.66 (m, 2H). HRMS(FAB) Calcd for C12H14FN3O5S 331.0638. Found
331.0639.
Compound 13g: 1H NMR (MeOD):
d 3.07 (s, 3H), 3.88 (t, 2H, J = 3.7 Hz),
4.03 (t, 2H, J = 5.4 Hz), 4.25–4.29 (m, 2H), 4.30–4.32 (m, 3H), 4.83–4.85
(m, 1H), 7.12 (d, 1H, J = 3.3 Hz), 7.41–7.48 (m, 1H), 7.63–7.68 (m, 1H).
HRMS(FAB) Calcd for C12H13FN6O4S 356.0703. Found 356.0705.
5. Barbachyn, M. R.; Ford, C. W. Angrew. Chem. 2003, 42, 2010.
6. (a) Gravestock, M. B.; David, G. A.; Betts, M. J.; Dennis, M.; Hatter, G.; McGregor,
A.; Swain, M. L.; Wilson, R. G.; Woods, L.; Wookey, A. Bioorg. Med. Chem. Lett.
2003, 13, 4179; (b) Philips, O. A.; Udo, E. E.; Ali, A. A. M.; Samuel, S. M. Bioorg.
Med. Chem. 2005, 13, 4113; (c) Jang, S. Y.; Ha, Y. H.; Ko, S. W.; Lee, W.; Lee, J.;
Kim, S.; Kim, Y. W.; Lee, W. K.; Ha, H. J. Bioorg. Med. Chem. Lett. 2004, 12, 3881;
(d) Lee, C. S.; Allwine, D. A.; Barbachyn, M. R.; Grega, K. C.; Dolak, L. A.; Ford, C.
W.; Jensen, R. M.; Seest, E. P.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H.;
Zurenko, G. E.; Genin, M. J. Bioorg. Med. Chem. 2001, 9, 3243.
Compound 14g: 1H NMR (MeOD):
d 3.90 (t, 2H, J = 3.3 Hz), 4.01 (t, 2H,
J = 6.0 Hz), 4.24–4.27 (m, 2H), 4.31–4.33 (m, 3H), 4.83–4.86 (m, 1H), 7.12
(d, 1H, J = 3.3 Hz), 7.42–7.48 (m, 1H), 7.63–7.68 (m, 1H). HRMS(FAB) Calcd
for C13H16FN3O7S2 409.0414. Found 409.0419.
Compound 15g: 1H NMR (CDCl3): d 1.86 (s, 3H), 3.20 (m, 2H), 3.47 (t, 2H,
J = 5.7 Hz), 3.70 (t, 2H, J = 6.0 Hz), 4.03 (t, 3H, J = 3.5 Hz), 4.73–4.78 (m, 1H), 5.30
(m, 1H), 7.20 (d, 1H, J = 3.1 Hz), 7.39 (t, 1H, J = 6.6 Hz), 7.58 (dd, 1H, J = 6.2 and
5.9 Hz). HRMS(FAB) Calcd for C14H17FN4O5S 372.0904. Found 372.0901.