Synthesis and antibacterial activity of derivatives of 6-O-allylic acylides

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 12, 2007, Pages 3330-3334

  Xu, Peng ^a   Liu, Lu ^a   Jin, Zhiping ^a   Lei, Pingsheng ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Acylide; Allylic; Macrolide; Resistant bacteria

Indexed keywords

3 O ACYL 6 O ALLYL 11,12 CARBONATE 5 O DESOSAMINYLERYTHRONOLIDE A; CETHROMYCIN; CLARITHROMYCIN; ERYTHROMYCIN; ERYTHRONOLIDE A; HYDROXYL GROUP; MACROLIDE; TEA 0777; TEA 0929; TELITHROMYCIN; UNCLASSIFIED DRUG;

ACYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES;

ACYLATION; ALKENES; ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; ERYTHROMYCIN; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MACROLIDES; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34249312995     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.03.107     Document Type: Article

References (24)

1. Asaka T., Manaka A., and Sugiyama H. Curr. Top. Med. Chem. 3 (2003) 961
2. Doern G., Heilmann K., and Huynh H. Antimicrob. Agents Chemother. 45 (2001) 1721
3. Pal S. Tetrahedron 62 (2006) 3171
4. Denis A., Agouridas C., Auger J.M., and Benedetti Y. Bioorg. Med. Chem. Lett. 9 (1999) 3075
5. Fogarty C., Buchanan P., Aubier M., Baz M., Van Resburg D., Rangaraju U., and Nusrat R. Int. J. Infect. Dis. 10 (2006) 136
6. Or Y.S., Clark R.F., Wang S., and Chu D.T.W. J. Med. Chem. 43 (2000) 1045
7. Keyes R., Carter J., and Englund E. J. Med. Chem. 46 (2003) 1795
8. Plata D., Leanna R., Rasmussen M., Mclaughliu M., Condon S., Kerdesky E., King S., Peterson M., Stoner E., and Wittenberger S. Tetrahedron 60 (2004) 10171
9. Agouridas C., Denis A., and Auger J.M. J. Med. Chem. 41 (1998) 4080
10. Ma Z., Clark R.F., Brazzale A., Plattner J., and Or Y.S. J. Med. Chem. 44 (2001) 4137
11. Misawa, Y.; Asaka, T.; Kashimura, M. WO Patent 9417088, 1994.
12. Asaka, T.; Misawa, Y.; Kashimura, M. WO Patent 9313115, 1993.
13. Asaka, T.; Misawa, Y.; Kashimura, M. WO Patent 9313116, 1993.
14. Tanikawa T., Asaka T., and Kashimura M. J. Med. Chem. 44 (2001) 4027
15. Tanikawa T., Asaka T., and Kashimura M. J. Med. Chem. 46 (2003) 2706
16. Nomura T., Yasukata T., and Narukawa Y. Bioorg. Med. Chem. 13 (2005) 6054
17. Stoner, E.; Peterson, M.; Ku, Y. U.S. Patent 6437106, 2002.
18. Or, Y. S.; Clark, R.; Ma, Z.; Chu, D. T. W.; Plattner, J. WO Patent 9809978, 1998.
19. Ma, Z.; Clark, R.; Wang, S.; Or, Y. S. 39th Interscience Conference on Antibacterial Agents and Chemotherapy, 1999, Abstract No. F2133.
20. Morimoto, S.; Adachi, T.; Matsunaga, T. U.S. Patent 4990602, 1991.
21. 13C NMR (ppm): 211.8, 173.3, 170.1, 154.0, 134.2, 134.1, 127.0, 126.7, 125.3, 118.0, 103.2, 84.7, 81.9, 80.3, 78.8, 78.7, 75.3, 70.2, 69.4, 65.8, 65.0, 45.1, 42.9, 40.2, 38.3, 37.4, 36.1, 35.4, 28.2, 22.2, 21.0, 20.3, 18.5, 14.9, 13.1, 12.8, 10.1, 9.0.
22. The MIC assays were performed in accordance with the NCCLS guidelines: Methods for dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 5th ed.; NCCLS Document M7-A5; NCCLS, January 2000; 20.
23. Performance Standards for Antimicrobial Susceptibility Testing: Eleventh Informational Supplement; NCCLS Document M100-S11; NCCLS, January 2001; 21, 1.
24. Amsterdam D. Susceptibility Testing of Antimicrobials in Liquid Media. Antibiotics in Laboratory Medicine. 4th ed. (1996), Williams & Wilkins, Baltimore, MD 52-111