Synthesis and antibacterial activity of novel 15-membered macrolide derivatives: 4″-Carbamate, 11,12-cyclic carbonate-4″-carbamate and 11,4″-di-O-arylcarbamoyl analogs of azithromycin

European Journal of Medicinal Chemistry

Volumn 44, Issue 10, 2009, Pages 4010-4020

  Ma, Shutao ^a   Ma, Ruixin ^b   Liu, Zhaopeng ^a   Ma, Chenchen ^a   Shen, Xuecui ^a  

^a SHANDONG UNIVERSITY   (China)

^b QINGDAO UNIVERSITY   (China)

Author keywords

15 Membered macrolide analogs; Antibacterial activity; Macrolide; Synthesis

Indexed keywords

11 O (2 CHLOROBENETHYLCARBAMOYL) 4'' O (4 HYDROXYPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (2 CHLOROPHENETHYLCARBAMOYL) 4'' O (4 FLUOROBENZYLCARBAMOYL)AZITHROMYCIN; 11 O (2 PENTYLCARBAMOYL) 4'' O (2 CHLOROPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (4 FLUOROBENZYLCARBAMOYL) 4'' O (2 CHLOROPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (4 HYDROXYPHENETHYLCARBAMOYL) 4'' O (2 CHLOROPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (BENZYLCARBAMOYL) 4'' O (2 CHLOROPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (BENZYLCARBAMOYL) 4'' O (4 HYDROXYPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (BUTYLCARBAMOYL) 4'' O (4 HYDROXYPHENETHYLCARBAMOYL)AZITHROMYCIN; 11 O (BUTYLCARBAMOYL) 4'' O (4 METHOXYBENZYLCARBAMOYL)AZITHROMYCIN; 11 O (PENTYLCARBAMOYL) 4'' O (4 METHOXYBENYLCARBAMOYL)AZITHROMYCIN; 11 O (PHENETHYLCARBAMOYL) 4'' O (4 FLUOROBENZYLCARBAMOYL)AZITHROMYCIN; 11,12 CYCLIC CARBONATE 4'' CARBAMATE DERIVATIVE; 2' O ACETYL 4'' O ACYLIMIDAZOLYLAZITHROMYCIN; 2' O ACETYLAZITHROMYCIN; 4'' CARBAMATE DERIVATIVE; 4'' O (2 CHLOROPHENETHYLCARBAMOYL)AZITHROMYCIN; 4'' O (3,4 METHYLENEDIOXYPHENETHYLCARBAMOYL)AZITHROMYCIN; 4'' O (4 FLUOROBENZYLCARBAMOYL)AZITHROMYCIN; 4'' O (4 HYDROXYPHENETHYLCARBAMOYL)AZITHROMYCIN; 4'' O (4 METHOXYBENZYLCARBAMOYL)AZITHROMYCIN; 4'' O (BENZYLCARBAMOYL)AZITHROMYCIN; 4'' O (BUTYLCARBAMOYL)AZITHROMYCIN; 4'' O (PHENETHYLCARBAMOYL)AZITHROMYCIN; 4'' O (PROPENYLCARBAMOYL)AZITHROMYCIN; 4'' O (PROPYLCARBAMOYL)AZITHROMYCIN; AZITHROMYCIN; CARBAMIC ACID DERIVATIVE; CLARITHROMYCIN; MACROLIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GENE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ERM GENE; MEF GENE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; STAPHYLOCOCCUS; STAPHYLOCOCCUS PNEUMONIAE; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; AZITHROMYCIN; CARBAMATES; CARBONATES; DRUG RESISTANCE, BACTERIAL; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS; STREPTOCOCCAL INFECTIONS; STREPTOCOCCUS PNEUMONIAE;

EID: 67651171212     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.04.030     Document Type: Article

References (21)

1. In: Omura S. (Ed). Macrolide Antibiotics: Chemistry, Biology, and Practice. second ed. (2002), Academic Press, London
2. In: Schoenfeld W., and Kirst H.A. (Eds). Macrolide Antibiotics (2002), Birkhaeuser, Basel
3. Itoh Z., Nakaya K., Suzuki H., Aria H., and Wakabayashi K. Am. J. Physiol. 247 (1984) G688-G694
4. 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
5. Katz L., Chu D.T.W., and Plattner J.J. J. Med. Chem. 39 (1996) 3853-3874
6. Lai C.J., and Weisblum B. Proc. Natl. Acad. Sci. U.S.A. 68 (1971) 856-860
7. Weisblum B. Antimicrob. Agents Chemother. 39 (1995) 577-585
8. 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
9. 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
10. Bryskier A. Clin. Infect. Dis. 27 (1998) 865-883
11. Hansen L.H., Mauvais P., and Douthwaite S. Mol. Microbiol. 31 (1999) 623-631
12. Champney W.S., and Tober C.L. Curr. Microbiol. 42 (2001) 203-210
13. Wu Y.J., and Su W.G. Curr. Med. Chem. 8 (2001) 1727-1758
14. Xu P., Liu L., Jin Z., Wang G., Liu J., Li Y., and Lei P. Bioorg. Med. Chem. Lett. 18 (2008) 5507-5511
15. Takashima H. Curr. Top. Med. Chem. 3 (2003) 991-999
16. Pal S. Tetrahedron 62 (2006) 3171-3200
17. Istuk Z.M., Mutak S., Kujundzic N., and Kragol G. Bioorg. Med. Chem. 15 (2007) 4498-4510
18. Miura T., Kanemoto K., Natsume S., Atsumi K., Fushimi H., Yoshida T., and Ajito K. Bioorg. Med. Chem. 16 (2008) 10129-10156
19. H. Cheng, M.A. Letavic, C.B. Ziegler, J.K. Dutra, P. Bertinato, B.S. Bronk, U.S. Patent 6,043,227, 2000.
20. Fernandes P.B., Baker W.R., Freiberg L.A., Hardy D.J., and McDonald E. J. Antimicrob. Agents Chemother. 33 (1989) 78-81
21. Champney W.S., and Tober C.L. Curr. Microbiol. 38 (1999) 342-348