메뉴 건너뛰기




Volumn 63, Issue 1, 2010, Pages 3-8

Synthesis and antibacterial activity of novel 11,12-cyclic carbonate azithromycin 4-O-carbamate derivatives

Author keywords

4 O carbamate derivatives; Antibacterial activity; Macrolides; Resistance; Synthesis

Indexed keywords

4'' O [[(2 CHLOROPHENETHYL)AMINO] 4 OXOBUTYL]CARBAMOYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 4'' O [[(3 CHLOROBENZYL)AMINO] 4 OXOBUTYL]CARBAMOYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 4'' O [[(4 HYDROXYPHENETHYL)AMINO] 4 OXOBUTYL]CARBAMOYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 4'' O [[(4 METHOXYBENZYL)AMINO] 4 OXOBUTYL]CARBAMOYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; 4'' O [[(PHENETHYL)AMINO] 4 OXOBUTYL]CARBAMOYLAZITHROMYCIN 11,12 CYCLIC CARBONATE; AZITHROMYCIN; CARBAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 76449114848     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2009.108     Document Type: Article
Times cited : (21)

References (19)
  • 1
    • 0021697495 scopus 로고
    • Erythromycin mimics exogenous motilin in gastrointestinal contractile activity in the dog
    • Itoh, Z., Nakaya, K., Suzuki, H., Aria, H. & Wakabayashi, K. Erythromycin mimics exogenous motilin in gastrointestinal contractile activity in the dog. Am. J. Physiol. 247, G688-G694 (1984).
    • (1984) Am. J. Physiol. , vol.247
    • Itoh, Z.1    Nakaya, K.2    Suzuki, H.3    Aria, H.4    Wakabayashi, K.5
  • 2
    • 0035059952 scopus 로고    scopus 로고
    • Review of macrolides and ketolides focus on respiratory tract infections
    • Zhanel, G. G. et al. Review of macrolides and ketolides focus on respiratory tract infections. Drugs 61, 443-498 (2001).
    • (2001) Drugs , vol.61 , pp. 443-498
    • Zhanel, G.G.1
  • 3
    • 0029796373 scopus 로고    scopus 로고
    • New directions in antibacterial research
    • Katz, L., Chu, D. T. W. & Plattner, J. J. New directions in antibacterial research. J. Med. Chem. 39, 3853-3874 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 3853-3874
    • Katz, L.1    Chu, D.T.W.2    Plattner, J.J.3
  • 4
    • 0015043629 scopus 로고
    • Altered methylation of ribosomal RNA in an erythromycinresistant strain of Staphylococcus aureus
    • Lai, C. J. & Weisblum, B. Altered methylation of ribosomal RNA in an erythromycinresistant strain of Staphylococcus aureus. Proc. Natl Acad. Sci. USA 68, 856-860 (1971).
    • (1971) Proc. Natl Acad. Sci. USA , vol.68 , pp. 856-860
    • Lai, C.J.1    Weisblum, B.2
  • 5
    • 0028963496 scopus 로고
    • Erythromycin resistance by ribosome modification
    • Weisblum, B. Erythromycin resistance by ribosome modification. Antimicrob. Agents Chemother. 39, 577-585 (1995).
    • (1995) Antimicrob. Agents Chemother. , vol.39 , pp. 577-585
    • Weisblum, B.1
  • 6
    • 0036343455 scopus 로고    scopus 로고
    • The ketolides: A critical review
    • Zhanel, G. G. et al. The ketolides: a critical review. Drugs 62, 1771 - 1804 (2002).
    • (2002) Drugs , vol.62 , pp. 1771-1804
    • Zhanel, G.G.1
  • 7
    • 2442735449 scopus 로고    scopus 로고
    • Novelties in the field of anti-infectives in 1997
    • Bryskier, A. Novelties in the field of anti-infectives in 1997. Clin. Infect. Dis. 27, 865-883 (1998).
    • (1998) Clin. Infect. Dis. , vol.27 , pp. 865-883
    • Bryskier, A.1
  • 8
    • 0032904341 scopus 로고    scopus 로고
    • A ketolide resistance mutation in domain II of 23S rRNA reveals the proximity of hairpin 35 to the peptidyl transferase centre
    • Xiong, L., Shah, S., Mauvais, P. & Mankin, A. S. A ketolide resistance mutation in domain II of 23S rRNA reveals the proximity of hairpin 35 to the peptidyl transferase centre. Mol. Microbiol. 31, 633-639 (1999).
    • (1999) Mol. Microbiol. , vol.31 , pp. 633-639
    • Xiong, L.1    Shah, S.2    Mauvais, P.3    Mankin, A.S.4
  • 9
    • 0032950956 scopus 로고    scopus 로고
    • The macrolide-ketolide antibiotic binding site is formed by structures in domains II and v of 23S ribosomal RNA
    • Hansen, L. H., Mauvais, P. & Douthwaite, S. The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA. Mol. Microbiol. 31, 623-631 (1999).
    • (1999) Mol. Microbiol. , vol.31 , pp. 623-631
    • Hansen, L.H.1    Mauvais, P.2    Douthwaite, S.3
  • 10
    • 0035112554 scopus 로고    scopus 로고
    • Structure-activity relationships for six ketolide antibiotics
    • Champney, W. S. & Tober, C. L. Structure-activity relationships for six ketolide antibiotics. Curr. Microbiol. 42, 203-210 (2001).
    • (2001) Curr. Microbiol. , vol.42 , pp. 203-210
    • Champney, W.S.1    Tober, C.L.2
  • 11
    • 0035950132 scopus 로고    scopus 로고
    • Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria
    • Schlunzen, F. et al. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 413, 814-821 (2001).
    • (2001) Nature , vol.413 , pp. 814-821
    • Schlunzen, F.1
  • 12
    • 33644921212 scopus 로고    scopus 로고
    • A journey across the sequential development of macrolides and ketolides related to erythromycin
    • Pal, S. A journey across the sequential development of macrolides and ketolides related to erythromycin. Tetrahedron 62, 3171-3200 (2006).
    • (2006) Tetrahedron , vol.62 , pp. 3171-3200
    • Pal, S.1
  • 13
    • 0035173131 scopus 로고    scopus 로고
    • Recent developments on ketolides and macrolides
    • Wu, Y. J. & Su, W. G. Recent developments on ketolides and macrolides. Curr. Med. Chem. 8, 1727-1758 (2001).
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1727-1758
    • Wu, Y.J.1    Su, W.G.2
  • 14
    • 0024590644 scopus 로고
    • New macrolides active against Streptococcus pyogenes with inducible or constitutive type of macrolide-lincosamide-streptogramin B resistance
    • Fernandes, P. B., Baker, W., Freiberg, L. A., Hardy, D. & McDonald, E. New macrolides active against Streptococcus pyogenes with inducible or constitutive type of macrolide-lincosamide-streptogramin B resistance. Antimicrob. Agents Chemother. 33, 78-81 (1989).
    • (1989) Antimicrob. Agents Chemother. , vol.33 , pp. 78-81
    • Fernandes, P.B.1    Baker, W.2    Freiberg, L.A.3    Hardy, D.4    McDonald, E.5
  • 15
    • 0038474136 scopus 로고    scopus 로고
    • Structural consideration of macrolide antibiotics in relation to the ribosomal interaction and drug design
    • Takashima, H. Structural consideration of macrolide antibiotics in relation to the ribosomal interaction and drug design. Curr. Top. Med. Chem. 3, 991-999 (2003).
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 991-999
    • Takashima, H.1
  • 16
    • 0026527863 scopus 로고
    • Clarithromycin and azithromycin: New macrolide antibiotics
    • Piscitelli, S. C., Danziger, L. H. & Rodvold, K. A. Clarithromycin and azithromycin: new macrolide antibiotics. Clin. Pharm. 11, 137-152 (1992).
    • (1992) Clin. Pharm. , vol.11 , pp. 137-152
    • Piscitelli, S.C.1    Danziger, L.H.2    Rodvold, K.A.3
  • 17
    • 61349195336 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of 400,11-di-O-arylalkylcarbamoyl azithromycin derivatives that have activity against resistant strains
    • Ma, S. et al. Synthesis and antibacterial activity of 400,11-di-O-arylalkylcarbamoyl azithromycin derivatives that have activity against resistant strains. Bioorg. Med. Chem. Lett. 19, 1698-1701 (2009).
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1698-1701
    • Ma, S.1
  • 18
    • 67651171212 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of novel 15-membered macrolide derivatives: 400-carbamate 11,12-cyclic carbonate- 400-carbamate and 11,400-di-O-arylcarbamoyl analogs of azithromycin
    • Ma, S., Ma, R., Liu, Z., Ma, C. & Shen, X. Synthesis and antibacterial activity of novel 15-membered macrolide derivatives: 400-carbamate, 11,12-cyclic carbonate- 400-carbamate and 11,400-di-O- arylcarbamoyl analogs of azithromycin. Eur. J. Med. Chem. 44, 4010-4020 (2009).
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 4010-4020
    • Ma, S.1    Ma, R.2    Liu, Z.3    Ma, C.4    Shen, X.5
  • 19
    • 0038135144 scopus 로고    scopus 로고
    • Macrolide antibiotics: Binding site, mechanism of action, resistance
    • Marne, G. & Alexander, S. M. Macrolide antibiotics: binding site, mechanism of action, resistance. Curr. Top. Med. Chem. 3, 949-960 (2003).
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 949-960
    • Marne, G.1    Alexander, S.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.