Synthesis and antibacterial activity of novel 3-O-carbamoyl derivatives of clarithromycin and 11,12-cyclic carbonate azithromycin

European Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2010, Pages 915-922

  Zhang, Ling ^a   Song, Linchen ^a   Liu, Zhaopeng ^a   Li, Hui ^a   Lu, Yingdong ^a   Li, Zerong ^a   Ma, Shutao ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

3 O Descladinosylazithromycin derivative; 3 O descladinosylclarithromycin derivative; Antibacterial activity; Bacterial resistance; Synthesis

Indexed keywords

3 O [(2 CHLOROPHENETHYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(2 CHLOROPHENETHYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(3,4 METHYLENEDIOXYPHENETHY)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(4 FLUOROBENZYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(4 FLUOROBENZYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(4 HYDROXYPHENETHYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(4 METHOXYBENZYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(4 METHOXYBENZYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(BENZYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(BENZYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(BUTYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(BUTYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(PENTYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(PENTYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(PHENETHYL)CARBAMOYL] 3 O DESCLADINOSYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 3 O [(PHENETHYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(PROPENYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; 3 O [(PROPYL)CARBAMOYL] 3 O DESCLADINOSYLCLARITHROMYCIN; AZITHROMYCIN; CARBAMIC ACID DERIVATIVE; CLARITHROMYCIN; ERYTHROMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL GENE; CONTROLLED STUDY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ERM GENE; GENETIC CODE; IN VITRO STUDY; MEF GENE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; AZITHROMYCIN; CLARITHROMYCIN; DRUG EVALUATION, PRECLINICAL; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STREPTOCOCCUS PNEUMONIAE;

EID: 75849159202     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.11.032     Document Type: Article

References (23)

1. Washington II J.A., and Wilson W.R. Mayo Clin. Proc 60 (1985) 189-203
2. Washington II J.A., and Wilson W.R. Mayo Clin. Proc 60 (1985) 271-278
3. Atkins P.J., Herbert T.O., and Jones N.B. Int. J. Pharm. 30 (1986) 199-207
4. Itoh Z., Nakaya K., Suzuki H., Aria H., and Wakabayashi K. Am. J. Physiol. 247 (1984) G688-G694
5. Omura S., Tsuzuki K., Sunazuka T., Marui S., Toyoda H., Inatomi N., and Itoh Z. J. Med. Chem 30 (1987) 1943-1948
6. Zhanel G.G., Dueck M., Hoban D.J., Vercaigne L.M., Embil J.M., Gin A.S., and Karlowsky J.A. Drugs 61 (2001) 443-498
7. Katz L., Chu D.T.W., and Plattner J.J. J. Med. Chem 39 (1996) 3853-3874
8. Felmingham D., and Grüneberg R.N. J. Antimicrob. Chemother 45 (2000) 191-203
9. Lai C.J., and Weisblum B. Proc. Natl. Acad. Sci. USA 68 (1971) 856-860
10. Weisblum B. Antimicrob. Agents Chemother. 39 (1995) 577-585
11. Zhanel G.G., Walters M., Noreddin A., Vercaigne L.M., Wierzbowski A., Embil J.M., Gin A.S., Douthwaite S., and Hobanl D.J. Drugs 62 (2002) 1771-1804
12. Bax R.P., Anderson R., Crew J., Fletcher P., Johnson T., Kaplan E., Knaus B., Kristinsson K., Malek M., and Strandberg L. Nat. Med. 4 (1998) 545-546
13. Bryskier A. Clin. Infect. Dis. 27 (1998) 865-883
14. Hansen L.H., Mauvais P., and Douthwaite S. Mol. Microbiol. 31 (1999) 623-631
15. Champney W.S., and Tober C.L. Curr. Microbiol. 42 (2001) 203-210
16. Schlunzen F., Zarivach R., Harms J., Bashan A., Tocilj A., Albrecht R., Yonath A., and Franceschi F. Nature 413 (2001) 814-821
17. Pal S. Tetrahedron 62 (2006) 3171-3200
18. Tanikawa T., Asaka T., and Kashimura M. J. Med. Chem. 44 (2001) 4027-4030
19. Tanikawa T., Asaka T., Kashimura M., Suzuki K., Sugiyama H., Sato M., Kameo K., Morimoto S., and Nishida A. J. Med. Chem. 46 (2003) 2706-2715
20. Zhu B., Marinelli B.A., Abbanat D., Foleno B.D., Henninger T.C., Bush K., and Macielag M.J. Bioorg. Med. Chem. Lett. 16 (2006) 1054-1059
21. Xu P., Liu L., Jin Z., and Lei P. Bioorg. Med. Chem. Lett. 17 (2007) 3330-3334
22. Fernandes P.B., Baker W.R., Freiberg L.A., Hardy D.J., and McDonald E.J. Antimicrob. Agents Chemother. 33 (1989) 78-81
23. Champney W.S., and Tober C.L. Curr. Microbiol. 38 (1999) 342-348