Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: I. 4'', 11 and 12-OMe derivatives via direct methylation

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 5, 1998, Pages 549-554

  Waddell, Sherman T ^a   Santorelli, Gina M ^a   Blizzard, Timothy A ^a   Graham, Amy ^b   Occi, James ^b  

^a Departments of Medicinal Chemistry   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; AZALIDE ANTIBIOTIC; ERYTHROMYCIN; MACROLIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; METHYLATION; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ERYTHROMYCIN; GRAM-POSITIVE BACTERIA; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE;

EID: 0032478249     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00070-5     Document Type: Article

References (9)

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3. (c) Morimoto, S.; Nagate, T.; Sugita, K.; Ono, T.; Numata, K.; Miyachi, J.; Misawa, Y; Yamada, K; Omura, S. J. Antibiotics 1990, 43, 295.
4. 2. (a) Djokic, S.; Kobrehel, G.; Lazarevski, G.; Loppotar, N.; Tamburasev, Z.; Kamenar, B.; Nagel, A; Vickovic, I. J. Chem. Soc., Perkin Trans. I, 1986, 1881.
5. (b) Bright, G.; Nagel, A.; Bordner, J.; Desai, K.; Dibrino, J.; Nowakowska, J.; Vincent, L.; Watrous, R.; Sciavolino, F.; English, A.; Retsema, J.; Anderson, M.; Brennan, L.; Borovoy, R.; Cimchowski, C.; Faiella, J.; Girard, A.; Girard, D.; Herbert, C.; Manousos, M.; Mason, R. J. Antibiotics 1988, 41, 1029.
6. 3. Wilkening, R.; Ratcliffe, R.; Doss, G.; Bartizal, K.; Graham, A.; Herbert, C. Bioorg. Med. Chem. Lett., 1993, 6, 1287.
7. 4. Kobrehel, G.; Lazarevski, G.; Djokic, S.; Kolocny-Babic, L.; Kucisec-Tepes, N; Cvrlje, M. J. Antibiotics 1992, 45, 527.
8. 5. The synthesis of 6-OMe-9-deoxo-9a-aza-9a-homoerymromycin will be the subject of a subsequent report.
9. 13C NMR spectrum. Next, we found that in every case a very strong coupling is seen from the protons on a methoxy group to the carbon bearing that methoxy group. With a complete carbon assignment, this makes it a simple matter to determine the locations of the methoxy groups.