Synthesis and antibacterial activities of pleuromutilin derivatives

Chinese Chemical Letters

Volumn 20, Issue 1, 2009, Pages 29-31

  Zhang, Yuan Yuan ^a   Xu, Ke Ping ^a   Ren, Dan ^a   Ge, Shao Rong ^a   Wang, Yu Liang ^a   Wang, Yu Zhong ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Antibacterial activities; Derivatives; Pleuromutilin; Synthesis

Indexed keywords

EID: 57349131520     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2008.09.009     Document Type: Article

References (14)

1. Kavanagh F., Hervey A., and Robbins W.J. Proc. Natl. Acad. Sci. 37 (1951) 570
2. Nurse K., Sterner T., Ferguson D., et al. Nucl. Acids Symp. Ser. 41 (1999) 11
3. Egger H., and Reinshagen H. J. Antibiot. 29 (1976) 925
4. Drews J., Georgopoulos A., Laber G., et al. Antimicrob. Agents Chemother. 7 (1975) 507
5. Egger H., and Reinshagen H. J. Antibiot. 29 (1976) 923
6. H. Berner, H. Vyplel. EP 0153277 (1985).
7. Jones R.N., Fritsche T.R., Sader H.S., et al. Antimicrob. Agents Chemother. 50 (2006) 2583
8. I. Macher. US 5164526 (1992).
9. 3, δ ppm): 0.71 (d, 3H, J = 6.4 Hz), 0.88 (d, 3H, J = 7.2 Hz), 1.11-1.15 (m, 1H), 1.18 (s, 3H), 1.26 (s, 6H), 1.28 (t, 3H, J = 7.2 Hz), 1.33-1.37 (m, 1H), 1.40-1.43 (m, 1H), 1.46 (s, 3H), 1.49-1.51 (m, 1H), 1.52-1.57 (m, 1H), 1.61-1.69 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.8 Hz), 2.09-2.15 (m, 2H), 2.18-2.27 (m, 2H), 2.31-2.38 (m, 1H), 3.07-3.22 (m, 4H), 3.35 (d, 1H, J = 6.4 Hz), 4.10 (q, 2H, J = 7.2 Hz), 5.18 (dd, 1H, J = 17.2 Hz, 1.2 Hz), 5.33 (dd, 1H, J = 11.2 Hz, 1.2 Hz), 5.40 (t, 1H, J = 6.0 Hz), 5.75 (d, 1H, J = 8.4 Hz), 6.44 (dd, 1H, J = 17.2 Hz, 10.8 Hz); MS (HRESI) m/z: 536.3035 [M-H].
10. 3, δ ppm): 0.72 (d, 3H, J = 6.8 Hz), 0.89 (d, 3H, J = 7.2 Hz), 0.94 (d, 6H, J = 6.8 Hz), 1.12-1.16 (m, 1H), 1.17 (s, 3H), 1.26 (s, 6H), 1.33-1.37 (m, 1H), 1.41-1.44 (m, 1H), 1.47 (s, 3H), 1.48-1.50 (m, 1H), 1.52-1.55 (m, 1H), 1.62-1.70 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.8 Hz), 1.87-1.97 (m, 1H), 2.06-2.14 (m, 2H), 2.18-2.29 (m, 2H), 2.31-2.37 (m, 1H), 3.09-3.22 (m, 4H), 3.36 (d, 1H, J = 6.8 Hz), 3.85 (d, 2H, J = 6.8 Hz), 5.41 (t, 1H, J = 6.0 Hz), 5.20 (dd, 1H, J = 17.2 Hz, 1.2 Hz), 5.34 (dd, 1H, J = 10.8 Hz, 0.8 Hz), 5.75 (d, 1H, J = 8.0 Hz), 6.47 (dd, 1H, J = 17.2 Hz, 10.8 Hz); MS (HRESI) m/z: 564.3349 [M-H].
11. 3, δ ppm): 0.71 (d, 3H, J = 7.2 Hz), 0.88 (d, 3H, J = 7.2 Hz), 1.11-1.15 (m, 1H), 1.18 (s, 3H), 1.28 (s, 6H), 1.31-1.36 (m, 1H), 1.39-1.42 (m, 1H), 1.44 (s, 3H), 1.46-1.50 (m, 1H), 1.52-1.57 (m, 1H), 1.61-1.68 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.8 Hz), 2.04-2.16 (m, 2H), 2.19-2.29 (m, 2H), 2.33-2.37 (m, 1H), 3.14-3.31 (m, 4H), 3.36 (d, 1H, J = 6.4 Hz), 5.20 (dd, 1H, J = 17.6 Hz, 1.6 Hz), 5.35 (dd, 1H, J = 11.2 Hz, 1.2 Hz), 5.77 (d, 1H, J = 8.4 Hz), 5.93 (t, 1H, J = 6.0 Hz), 6.48 (dd, 1H, J = 17.6 Hz, 11.2 Hz), 7.11-7.15 (m, 2H), 7.18-7.22 (m, 1H), 7.34-7.38 (m, 2H); MS (HRESI) m/z: 584.3254 [M-H].
12. 1H NMR (400 MHz, CDCl3, δ ppm): 0.71 (d, 3H, J = 7.2 Hz), 0.88 (d, 3H, J = 7.2 Hz), 1.08-1.12 (m, 1H), 1.14 (s, 3H), 1.26 (s, 6H), 1.31-1.36 (m, 1H), 1.39-1.43 (m, 1H), 1.45 (s, 3H), 1.47-1.50 (m, 1H), 1.53-1.56 (m, 1H), 1.61-1.68 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.8 Hz), 2.04-2.12 (m, 2H), 2.15-2.28 (m, 2H), 2.31-2.37 (m, 1H), 3.11-3.25 (m, 4H), 3.35 (d, 1H, J = 6.4 Hz), 5.12 (s, 2H), 5.16 (d, 1H, J = 18.0 Hz), 5.29 (d, 1H, J = 10.8 Hz), 5.51 (t, 1H, J = 6.4 Hz), 5.74 (d, 1H, J = 7.6 Hz), 6.43 (dd, 1H, J = 17.2 Hz, 10.8 Hz), 7.33-7.38 (m, 5H); MS (HRESI) m/z: 598.3172 [M-H].
13. 1H NMR (400 MHz, CDCl3, δ ppm): 0.72 (d, 3H, J = 6.8 Hz), 0.88 (d, 3H, J = 7.2 Hz), 1.11-1.14 (m, 1H), 1.15 (s, 3H), 1.22-1.25 (m, 1H), 1.31-1.34 (m, 1H), 1.36 (s, 6H), 1.45 (s, 3H), 1.47-1.52 (m, 1H), 1.54-1.56 (m, 1H), 1.61-1.70 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.4 Hz), 2.02-2.11 (m, 2H), 2.14-2.24 (m, 2H), 2.30-2.36 (m, 1H), 3.22 (s, 2H), 3.35 (d, 1H, J = 6.4 Hz), 3.65 (s, 2H), 5.18 (dd, 1H, J = 17.2 Hz, 1.2 Hz), 5.31 (dd, 1H, J = 10.8 Hz, 1.2 Hz), 5.75 (d, 1H, J = 8.4 Hz), 6.48 (dd, 1H, J = 17.2 Hz, 10.8 Hz), 6.90 (d, 1H, J = 9.2 Hz), 7.40 (dd, 1H, J = 10 Hz, 2.4 Hz), 7.42 (d, 1H, J = 2.4 Hz), 8.29 (s, 1H); MS (HRESI) m/z: 646.2237, 648.2218 [M-H, isotope peaks].
14. 1H NMR (400 MHz, CDCl3, δ ppm): 0.71 (d, 3H, J = 6.8 Hz), 0.88 (d, 3H, J = 7.2 Hz), 1.09-1.12 (m, 1H), 1.14 (s, 3H), 1.25-1.29 (m, 1H), 1.32-1.35 (m, 1H), 1.37 (s, 6H), 1.47 (s, 3H), 1.48-1.51 (m, 1H), 1.53-1.58 (m, 1H), 1.62-1.70 (m, 2H), 1.78 (dd, 1H, J = 14.4 Hz, 2.4 Hz), 2.06-2.16 (m, 2H), 2.19-2.27 (m, 2H), 2.32-2.36 (m, 1H), 3.21 (s, 2H), 3.36 (d, 1H, J = 6.8 Hz), 3.67 (s, 2H), 5.18 (dd, 1H, J = 17.2 Hz, 1.2 Hz), 5.31 (dd, 1H, J = 10.8 Hz, 1.2 Hz), 5.74 (d, 1H, J = 8.4 Hz), 6.47 (dd, 1H, J = 17.2 Hz, 10.8 Hz), 7.36 (d, 1H, J = 2.4 Hz), 7.71 (d, 1H, J = 2.4 Hz), 8.24 (s, 1H); MS (HRESI) m/z: 724.1336, 726.1323, 728.1317 [M-H, isotope peaks].