Synthesis and structure-activity relationship of a novel class of 15-membered macrolide antibiotics known as '11a-azalides'

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 19, 2012, Pages 5787-5801

  Sugimoto, Tomohiro ^a   Tanikawa, Tetsuya ^a   Suzuki, Keiko ^a   Yamasaki, Yukiko ^a  

^a TAISHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Azalide; Erythromycin resistant; Macrolactonization; Macrolide antibiotics

Indexed keywords

AZALIDE DERIVATIVE; AZIDE; AZITHROMYCIN; CARBAMIC ACID DERIVATIVE; CARBON; CETHROMYCIN; CLARITHROMYCIN; ERYTHROMYCIN; MACROLIDE; TELITHROMYCIN; UNCLASSIFIED DRUG;

AMINATION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GEL CHROMATOGRAPHY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; IN VITRO STUDY; MACROLACTONIZATION; MASS SPECTROMETRY; METHODOLOGY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; OXIDATIVE STRESS; PHOTON CORRELATION SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, BACTERIAL; ERYTHROMYCIN; HUMANS; MACROLIDES; PNEUMOCOCCAL INFECTIONS; RESPIRATORY TRACT INFECTIONS; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

STREPTOCOCCUS PNEUMONIAE;

EID: 84866434383     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.08.007     Document Type: Article

References (48)

1. S. Omura Macrolide Antibiotics. Chemistry, Biology, and Practice 2nd ed. 2002 Academic Press
2. T. Kaneko, T.J. Dougherty, and T.V. Magee Macrolide Antibiotics J.B. Taylor, D.J. Triggle, Comprehensive Medicinal Chemistry II Vol. 7 2006 Elsevier Ltd Oxford, UK 973
3. J.M. Blondeau Expert Opin. Pharmacother. 3 2002 1131
4. J.M. Blondeau, E. DeCarolis, K.L. Metzer, and G.T. Hansen Expert Opin. Investig. Drugs 11 2002 189
5. P. Kurath, P.H. Jones, R.S. Egan, and T.J. Perun Experientia 27 1971 362
6. J.T. Wilson, and C.J. van Boxtel Antibiot. Chemother. 25 1978 181
7. S. Morimoto, Y. Takahashi, Y. Watanabe, and S. Omura J. Antibiot. 37 1984 187
8. S. Djokić, G. Kobrehel, G. Lazarevski, N. Lopotar, and Z. Tamburasě v J. Chem. Soc., Perkin Trans. 1 1986 1881
9. G.V. Doern, K.P. Heilmann, H.K. Huynh, P.R. Rhomberg, S.L. Coffman, and A.B. Brueggemann Antimicrob. Agents Chemother. 45 2001 1721
10. D.J. Hoban, and G.G. Zhanel Expert Rev. Anti Infect. Ther. 4 2006 973 980
11. S.G. Jenkins, S.D. Brown, and D.J. Farrell Ann. Clin. Microbiol. Antimicrob. 7 2008 1
12. D. Felmingham, R. Cantón, and S.G. Jenkins J. Infect. 55 2 2007 111
13. B. Weisblum Antimicrob. Agents Chemother. 39 1995 577
14. M.C. Roberts, J. Sutcliffe, P. Courvalin, L.B. Jensen, J. Rood, and H. Seppala Antimicrob. Agents Chemother. 43 1999 2823
15. D.J. Farrell, I. Morrissey, S. Bakker, and D. Felmingham Antimicrob. Agents Chemother. 1 2002 39
16. A. Denis, C. Agouridas, J.-M. Auger, Y. Benedetti, A. Bonnefoy, F. Bretin, J.-F. Chantot, A. Dussarat, C. Fromentin, S.G. D'Ambrieres, S. Lachaud, P. Laurin, O.L. Martret, V. Loyau, N. Tessot, J.-M. Pejac, and S. Perron Bioorg. Med. Chem. Lett. 9 1999 3075
17. Y.S. Or, R.F. Clark, S. Wang, D.T.W. Chu, A.M. Nilius, R.K. Flamm, M. Mitten, P. Ewing, J. Alder, and Z. Ma J. Med. Chem. 43 2000 1045
18. Z. Ma, R.F. Clark, A. Brazzale, S. Wang, M.J. Rupp, L. Li, G. Griesgraber, S. Zhang, H. Yong, L.T. Phan, P.A. Nemoto, D.T.W. Chu, J.J. Plattner, X. Zhang, P. Zhong, Z. Cao, A.M. Nilius, V.D. Shortridge, R. Flamm, M. Mitten, J. Meulbroek, P. Ewing, J. Alder, and Y.S. Or J. Med. Chem. 44 2001 4137
19. L.T. Phan, R.F. Clark, M. Rupp, Y.S. Or, D.T.W. Chu, and Z. Ma Org. Lett. 2 2000 2951
20. R.F. Keyes, J.J. Carter, E.E. Englund, M.M. Daly, G.G. Stone, A.M. Nilius, and Z. Ma J. Med. Chem. 46 2003 1795
21. B. Zhu, B.A. Marinelli, D. Abbanat, B.D. Foleno, K. Bush, and M.J. Macielag Bioorg. Med. Chem. Lett. 17 2007 3900
22. M.A. Tennakoon, T.C. Henninger, D. Abbanat, B.D. Foleno, J.J. Hilliard, K. Bush, and M. Macielag Bioorg. Med. Chem. Lett. 16 2006 6231
23. T. Kaneko, H. McArthur, and J. Sutcliffe Expert Opin. Ther. Patents 10 2000 403
24. T. Asaka, A. Manaka, and H. Sugiyama Curr. Top. Med. Chem. 3 2003 961
25. S. Pal Tetrahedron 62 2006 3171
26. S.J. Shaw, D. Abbanat, G.W. Ashley, K. Bush, B. Foleno, M. Macielag, D. Zhang, and D.C. Myles J. Antibiot. 58 2005 167
27. G.W. Ashley, M. Burlingame, R. Desai, H. Fu, T. Leaf, P.J. Licari, C. Tran, D. Abbanat, K. Bush, and M. Macielag J. Antibiot. 59 2006 392
28. S.T. Waddell, and T.A. Blizzard Tetrahedron Lett. 34 1993 5385
29. S.T. Waddell, J.M. Eckert, and T.A. Blizzard Heterocycles 43 1996 2325
30. A. Nishida, K. Yagi, N. Kawahara, M. Nishida, and O. Yonemitsu Tetrahedron Lett. 36 1995 3215
31. T. Miura, K. Kanemoto, S. Natsume, K. Atsumi, H. Fushimi, T. Yoshida, and K. Ajito Bioorg. Med. Chem. 16 2008 10129
32. T. Sugimoto, and T. Tanikawa Med. Chem. Lett. 2 2011 234
33. O. Mitsunobu Synthesis 1981 1
34. T.C. Henninger, X. Xu, D. Abbanat, E.Z. Baum, B.D. Foleno, J.J. Hilliard, K. Bush, D.J. Hlasta, and M. Macielag Bioorg. Med. Chem. Lett. 14 2004 4495
35. E.H. Massey, B. Kitchell, L.D. Martin, K. Gerson, and H.W. Murphy Tetrahedron Lett. 2 1970 157
36. E. Wildsmith Tetrahedron Lett. 1972 29
37. P.H. Jones, T.J. Perun, E.K. Rowley, and E.J. Baker J. Med. Chem. 15 1972 631
38. M. Mizuno, and T. Shioiri Chem. Commun. 22 1997 2165
39. S. Ma, B. Jiao, Y. Ju, M. Zheng, R. Ma, L. Liu, L. Zhang, X. Shen, C. Ma, Y. Meng, H. Wang, Y. Qi, X. Ma, and W. Cui Eur. J. Med. Chem. 46 2011 556
40. Y. Ju, R. Xian, L. Zhang, R. Ma, J. Cao, and S. Ma Bioorg. Med. Chem. Lett. 20 2010 3272
41. Su, W. G.; Smyth, K. T.; Rainville, J. P.; Kaneko, T.; Sutcliffe, J. A.; Brennan, L. A.; Duignan, J. M.; Girard, A. E.; Finegan, S. M.; Cimochowski, C. R. In Presented at 38th Intersci. Conf. Antimicrob. Agents Chemother.; (Sept. 24-27, San Dieg). Abstr. No. F-122.
42. R. Faghih, M. Buytendorp, R. Stephens, D. Hardy, J. Plattner, and P. Lartey J. Antibiot. 43 1990 1334
43. D.D. Keith, S. De Bernardo, and M. Weigele Tetrahedron 31 1975 2629
44. J. Danklmaier, and H. Hoenig Liebigs Ann. Chem. 9 1988 851
45. K. Neimert-Andersson, E. Blomberg, and P. Somfai J. Org. Chem. 69 2004 3746
46. M. Tiecco, L. Testaferri, A. Temperini, L. Bagnoli, F. Marini, and C. Santi Chem. Eur. J. 10 2004 1752
47. M. Suhartono, A.E. Schneider, G. Dürner, and M.W. Göbel Synthesis. 2 2010 293
48. J.A. Frick, J.B. Klassen, A. Bathe, J.M. Abramson, and H. Rapoport Synthesis 1992 621