Synthesis of 6-O-methyl-azithromycin and its ketolide analogue via Beckmann rearrangement of 9(E)-6-O-methyl-erythromycin oxime

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 18, 1998, Pages 2427-2432

  Denis, A ^a   Agouridas, C ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6 O METHYLAZITHROMYCIN; AZITHROMYCIN; CLARITHROMYCIN; KETOLIDE; MACROLIDE; TELITHROMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HAEMOPHILUS INFLUENZAE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; AZITHROMYCIN; ERYTHROMYCIN; ESCHERICHIA COLI; HAEMOPHILUS INFLUENZAE; KETOLIDES; MACROLIDES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032558476     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00402-8     Document Type: Article

References (20)

1. [1] Chantot, J-F.; Bryskier, A.; Gasc, J-C. J. Antibiot. 1986, 39, 660-668.
2. b) Gasc, J. C.; Gouin d'Ambrières, S.; Lutz, A.; Chantot, J. F. J. Antibiotics 1991, 44, 313-330.
3. [2] Morimoto, S.; Takahashi, Y.; Watanabe, Y, Omura, S. J. Antibiotics 1984, 37, 187-189.
4. b) Morimoto, S.; Adachi, T.; Takahashi, Y.; Asaka, T.; Kashimura, M.; Watanabe, Y.; Omura, S.; Sota, K. New macrolide antibiotic. TE-031(A-56268); synthesis and biological properties. 26h Interscience Conference on Antimicrobial Agents and Chemotherapy, 1986, Abstr. No. 409.
5. c) Watanabe, Y.; Adachi, T.; Asaka, T.; Kashimura, M.; Morimoto, S. Heterocycles, 1990, 31, 2121-2124.
6. [3] Djokic, S.; Kobrehel, G.; Lazarevski, G.; Lopotar, N.; Tamburasev, Z. Erythromycin Series. Part II. Ring Expansion of Erythromycin A Oxime by the Beckmann Rearrangement. J. Chem. Soc. Prekin Trans. 1 1986, 1881-1890.
7. b) Djokic, S.; Kobrehel, G.; Lazarevski, G. Erythromycin series XII. J. Antibiotics 1987, 40, 1006-1015.
8. c)Bright, G. M.; Nagel, A. A.; Bordner, J.; Desai, K. A.; Dibrino, J. N.; Nowakowska, J.; Vincent, L.; Watrous, R. M.; Sciavolino, F. C.; English, A. R.; Retsema, J. A.; Anderson, M. R.; Brennan, L. A.; Borovoy, R. J.; Cimochowsky, C. R.; Fiaella, J. A.; Girard, A. E.; Girard, D.; Herbert, C.; Manousos, M.; Mason, R. J. Antibiotics 1988, 41, 1029-1047.
9. [4] Previous works concerning the ketolides were presented during the following meetings: a) Agouridas, C.; Benedetti, Y.; Denis, A.; Fromentin, C.; Gouin d'Ambrieres, S.; Le Martret, O.; Chantot, J-F. Ketolides, A New Distinct Semi-synthetic Class of Macrolides. 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1994, Abstr. No. F-164.
10. b) Agouridas, C.; Benedetti, Y.; Denis, A.; Le Martret, O.; Chantot, J-F. Ketolides: A New Distinct Class of Macrolide Antibacterials. Synthesis and Structural Characteristics of RU 004.35th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1995, Abstr. No. F-157.
11. [5] a) Agouridas, C.; Bonnefoy, A.; Chantot, J.-F.; In vitro Antibacterial Activity of HMR 3647, A Novel Ketolide Highly Active Against respiratory Pathogens. 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1997, Abstr. No. F-112.
12. b) Jones, R. N.; Biedenbach, D. J. Diagn. Microbiol. Infect. Dis., 1997, 27, 7-12.
13. [6] Kobrehel, G.; Lazarevski, G.; Djokic, S.; Kolacny-Babic, L. J. Antibiotics, 1992, 45, 527-534.
14. [7] Waddell, S. T.; Santorelli, G. M.; Blizzard, T. A.; Graham, A.; Occi, J. Bioorg. Med. Chem. Lett., 1998, 8, 549-554.
15. [8] a)Yang, B. V.; Goldsmith, M.; Rizzi, J. P. Tetrahedron Lett. 1994, 35, 3025-3028.
16. b) Wilkening, R.R.; Ratcliffe, R. W.; Doss, G. A.; Mosley, R. T.; Ball, R. G. Tetrahedron, 1997, 16923-16944.
17. [9] In the course of publication of our work on the aza-ketolide synthesis, a communication describing the synthesis of 8a-and 9a-azalides (including 2) from Beckmann rearrangement of 9(E) or (Z)-6-O-methyl-erythromycin oxime was published. Waddell, S. T.; Santorelli, G. M.; Blizzard, T. A.; Graham, A.; Occi, J. Bioorg. Med. Chem. Lett., 1998, 8, 1321-1326.
18. [10] Wilkening, R.R.; Ratcliffe, R. W.; Doss, G. A.; Bartizal, K. F.; Graham, A. C.; Herbert, C. M. Bioorg. Med. Chem. Lett. 1993, 3, 1287-1292.
19. [11] Molecular Modeling of 4 and its 12-9 isomeric imino-ether were carried out by using Insight II® (MSI corporation, San Diego, CA) software.
20. 9: C 61.76, H 9.69, N 4.64. Found : C 61.8, H 9.8, N 4.9.