7-Phenylplatensimycin and 11-methyl-7-phenylplatensimycin: More potent analogs of platensimycin

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 7, 2010, Pages 2156-2158

  Jang, Ki Po ^a   Kim, Chan Hyuk ^a   Na, Seong Wook ^a   Jang, Dong Seok ^a   Kim, Hiyoung ^a   Kang, Heonjoong ^a   Lee, Eun ^a  

^a Seoul National University   (South Korea)

Author keywords

11 Methyl 7 phenylplatensimycin; 7 Phenylplatensimycin; Antibiotic; Platensimycin

Indexed keywords

11 BROMOPLATENSIMYCIN; 11 CHLOROPLATENSIMYCIN; 11 METHYL 7 PHENYLPLATENSIMYCIN; 11 METHYLPLATENSIMYCIN; 15 PHENYL 17 NORPLATENSIMYCIN; 7 METHYLPLATENSIMYCIN; 7 PHENYLPLATENSIMYCIN; ANTIBIOTIC AGENT; CARBONYL DERIVATIVE; OXACILLIN; PLATENSIMYCIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ALKYLATION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; CONTROLLED STUDY; CYCLOADDITION; DRUG POTENCY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; HYDROLYSIS; NONHUMAN; STAPHYLOCOCCUS AUREUS; SUBSTITUTION REACTION;

ADAMANTANE; AMINOBENZOIC ACIDS; ANILIDES; ANTI-BACTERIAL AGENTS; ENTEROCOCCUS; GRAM-POSITIVE BACTERIA; GRAM-POSITIVE BACTERIAL INFECTIONS; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77949486958     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.02.037     Document Type: Article

References (33)

1. Wang J., et al. Nature 441 (2006) 358
2. Singh S.B., Jayasuriya H., Ondeyka J.G., Herath K.B., Zhang C., Zink D.L., Tsou N.N., Ball R.G., Basilio A., Genilloud O., Diez M.T., Vicente F., Pelaez F., Young K., and Wang J. J. Am. Chem. Soc. 128 (2006) 11916
3. Pearson H. Nature 441 (2006) 260
4. Brown E.D. Nature 441 (2006) 293
5. Häbich D., and von Nussbaum F. ChemMedChem 1 (2006) 951
6. Singh S.B., Herath K.B., Wang J., Tsou N., and Ball R.G. Tetrahedron Lett. 48 (2007) 5429
7. For a recent report compromising the use of FASII-based antimicrobials for treating sepsis caused by Gram-positive pathogens, see:. Brinster S., Lamberet G., Staels B., Trieu-Cuot P., Gruss A., and Poyart C. Nature 458 (2009) 83
8. For the first total synthesis, see:. Nicolaou K.C., Li A., and Edmonds D.J. Angew. Chem., Int. Ed. 45 (2006) 7086
9. For asymmetric total synthesis, see:. Nicolaou K.C., Edmonds D.J., Li A., and Tria G.S. Angew. Chem., Int. Ed. 46 (2007) 3942
10. Ghosh A.K., and Xi K. J. Org. Chem. 74 (2009) 1163
11. Nicolaou K.C., Li A., Edmonds D.J., Tria G.S., and Ellery S.P. J. Am. Chem. Soc. 131 (2009) 16905
12. For asymmetric formal synthesis, see:. Li P., Payette J.N., and Yamamoto H. J. Am. Chem. Soc. 129 (2007) 9534
13. Lalic G., and Corey E.J. Org. Lett. 9 (2007) 4921
14. Nicolaou K.C., Pappo D., Tsang K.Y., Gibe R., and Chen D.Y.-K. Angew. Chem., Int. Ed. 47 (2008) 944
15. Kim C.H., Jang K.P., Choi S.Y., Chung Y.K., and Lee E. Angew. Chem., Int. Ed. 47 (2008) 4009
16. Yun S.Y., Zheng J.-C., and Lee D. J. Am. Chem. Soc. 131 (2009) 8413
17. Nicolaou K.C., Li A., Ellery S.P., and Edmonds D.J. Angew. Chem., Int. Ed. 48 (2009) 6293
18. For racemic formal synthesis, see:. Zou Y., Chen C.-H., Taylor C.D., Foxman B.M., and Snider B.B. Org. Lett. 9 (2007) 1825
19. Nicolaou K.C., Tang Y., and Wang J. Chem. Commun. (2007) 1922
20. Tiefenbacher K., and Mulzer J. Angew. Chem., Int. Ed. 46 (2007) 8074
21. Matsuo J.-i., Takeuchi K., and Ishibashi H. Org. Lett. 10 (2008) 4049
22. McGrath N.A., Bartlett E.S., Sittihan S., and Njardarson J.T. Angew. Chem., Int. Ed. 48 (2009) 8543
23. For a recent review on the synthesis of platensimycin, see:. Tiefenbacher K., and Mulzer J. Angew. Chem., Int. Ed. 47 (2008) 2548
24. Nicolaou K.C., Chen J.S., Edmonds D.J., and Estrada A.A. Angew. Chem., Int. Ed. 48 (2009) 660
25. For some notable examples, see:. Nicolaou K.C., Lister T., Denton R.M., Montero A., and Edmonds D.J. Angew. Chem., Int. Ed. 46 (2007) 4712
26. Nicolaou K.C., Tang Y., Wang J., Stepan A.F., Li A., and Montero A. J. Am. Chem. Soc. 129 (2007) 14850
27. Nicolaou K.C., Stepan A.F., Lister T., Li A., Montero A., Tria G.S., Turner C.I., Tang Y., Wang J., Denton R.M., and Edmonds D.J. J. Am. Chem. Soc. 130 (2008) 13110
28. Yeung Y.-Y., and Corey E.J. Org. Lett. 10 (2008) 3877
29. Krauss J., Knorr V., Manhardt V., Scheffels S., and Bracher F. Arch. Pharm. Chem. Life Sci. 341 (2008) 386
30. Shen H.C., Ding F.-X., Singh S.B., Parthasarathy G., Soisson S.M., Ha S.N., Chen X., Kodali S., Wang J., Dorso K., Tata J.R., Hammond M.L., MacCoss M., and Colletti S.L. Bioorg. Med. Chem. Lett. 19 (2009) 1623
31. Wang J., Lee V., and Sintim H.O. Chem. Eur. J. 15 (2009) 2747
32. Jang K.P., Kim C.H., Na S.W., Kim H., Kang H., and Lee E. Bioorg. Med. Chem. Lett. 19 (2009) 4601
33. This analog has already been reported in Ref. 3f.