Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 23, 2011, Pages 7281-7298

  Kapić, Samra ^a   Čipčić Paljetak, Hana ^a   Palej Jakopović, Ivana ^a   Fajdetić, Andrea ^a   Ilijaš, Marina ^a   Štimac, Vlado ^a   Brajša, Karmen ^a   Holmes, David J ^b   Berge, John ^a   Alihodžić, Sulejman ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b GLAXOSMITHKLINE   (United States)

Author keywords

Antimicrobial activity; Macrolides; Piperazine; Quinolone; Structure activity relationship

Indexed keywords

1 ETHYL 4 OXO 6 [3 (1 PIPERAZINYL) 1 PROPYN 1 YL] 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; 1,1 DIMETHYLETHYL 4 (2 PROPYN 1 YL) PIPERAZINECARBOXYLATE; 4 O [3 [4 [3 ( 3 CARBOXY 1 ETHYL 4 OXO 1,4 DIHYDRO 6 QUINOLINYL) 2 PROPEN 1 YL] 1 PIPERAZINYL]PROPYL] 9 DEOXO 9A METHYL 9A AZA 9A HOMOERYTHROMYCIN A; 4 O [3 [4 [3 ( 3 CARBOXY 1 ETHYL 4 OXO 1,4 DIHYDRO 6 QUINOLINYL)PROPYL] 1 PIPERAZINYL]PROPYL] 9 DEOXO 9A METHYL 9A AZA 9A HOMOERYTHROMYCIN A; 4 O [3 [4 [3 (1 CYCLOPROPYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROPYL]PIPERAZINE 1 YL]PROPYONYL] 6 O METHYL ERYTHROMYCIN A; 4 O [3 [4 [3 (1 CYCLOPROPYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLYN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 6 O METHYL ERYTHROMYCIN A; 4 O [3 [4 [3 (1 ETHYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROPYL]PIPERAZINE 1 YL]PROPYONYL] 6 O METHYL ERYTHROMYCIN A; 4 O [3 [4 [4 (1 ETHYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLYN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 6 O METHYL ERYTHROMYCIN A; 6 [3 [4 [[(1,1 DIMETHYLETHYL)OXY]CARBONYL] 1 PIPERAZINYL]1 PROPYN 1 YL] 1 ETHYL 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLIC ACID; 9 DEOXO 4 O [3 [4 [3 (1 CYCLOPROPYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 CYCLOPROPYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROPYL]PIPERAZINE 1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 ETHYL 3 CARBOXY 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 ETHYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 ETHYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROPYL]PIPERAZINE 1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 ETHYL 3 ETHOXYCARBOXY 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROP 2 YNYL]PIPERAZINE 1 YL]PROPYONYL] 9A METHYL 9A AZA 9A HOMOERYTHROMYCIN A; 9 DEOXO 4 O [3 [4 [3 (1 TYL 3 ETHOXYCARBONYL 1,4 DIHYDRO 4 OXO QUINOLIN 6 YL)PROPYL]PIPERAZINE1 YL]PROPYONYL] 9A,11 O DIMETHYL 9A AZA 9A HOMOERYTHROMYCIN A; ANTIINFECTIVE AGENT; AZITHROMYCIN; CLARITHROMYCIN; ETHYL 1 CYCLOPROPYL 4 OXO 6 [3 (1 PIPERAZINYL) 1 PROPYN 1 YL] 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 1 CYCLOPROPYL 6 [3 [4 [[(1,1 DIMETHYLETHYL)OXY]CARBONYL] 1 PIPERAZINYL] 1 PROPYN 1 YL] 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 1 ETHYL 4 OXO 6 [3 (1 PIPERAZINYL) 1 PROPEN 1 YL] 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 1 ETHYL 4 OXO 6 [3 (1 PIPERAZINYL) 1 PROPYN 1 YL] 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 1 ETHYL 6 (3 HYDROXYL 1 PROPYN 1 YL) 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 6 [3 [4 [[(1,1 DIMETHYLETHYL)OXY]CARBONYL] 1 PIPERAZINYL] 1 PROPEN 1 YL] 1 ETHYL 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 6 [3 [4 [[(1,1 DIMETHYLETHYL)OXY]CARBONYL] 1 PIPERAZINYL] 1 PROPYN 1 YL] 1 ETHYL 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; ETHYL 6 [3 [[[(1,1 DIMETHYLETHYL)OXY]CARBONYL]OXY] 1 PROPEN 1 YL] 1 ETHYL 4 OXO 1,4 DIHYDRO 3 QUINOLINECARBOXYLATE; MACROLIDE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYNYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HAEMOPHILUS INFLUENZAE; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; MORAXELLA CATARRHALIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; MACROLIDES; PIPERAZINES; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80655146739     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.07.010     Document Type: Article

References (37)

1. A. Bryskier Clin. Microbiol. Infect. 6 2000 661
2. G.G. Zhanel, M. Dueck, D.J. Hoban, L.M. Vercaigne, J.M. Embil, A.S. Gin, and J.A. Karlowsky Drugs 61 2001 443
3. Agouridas, C.; Benedetti, Y.; Le Martret, O.; Chantot, J.-F. 35th Interscience Conference of Antimicrobial Agents and Chemotherapy, San Francisco, CA, 1995, Abstract No. F157.
4. C. Agouridas, A. Denis, J.-M. Augar, Y. Benedetti, A. Bonnefoy, F. Bretin, J.-F. Chantot, A. Dussarat, C. Fromentin, S.G. D′Ambrieres, S. Lachaud, P. Laurin, O. Le Martret, V. Loyan, and N.J. Tessot J. Med. Chem. 41 1998 4080
5. A. Bryskier, and A. Denis Ketolides: Novel Antibacterial Agents Designed to Overcome Resistance to Erythromycin A within Gram-Positive Cocci W. Schoenfeld, H.A. Kirst, Macrolide Antibiotics 2002 Brinkauser Verlag Basel 97
6. A. Bonnefoy, A.M. Girard, C. Agouridas, and J.F. Chantot J. Antimicrob. Chemother. 40 1997 85
7. M. Matanović Škugor, V. Štimac, I. Palej Jakopović, D. Lugarić, H. Čipčić Paljetak, D. Filić, M. Modrić, I. ilović, D. Gembarovski, S. Mutak, V. Eraković Haber, D.J. Holmes, Z. Ivezić Schoenfeld, and S. Alihodžić Bioorg. Med. Chem. 18 2010 6547
8. A. Hutinec, M. Djerek, G. Lazarevski, V. Šunjić, H. Čipčić Paljetak, S. Alihodžić, V. Eraković Haber, M. Dumić, and S. Mutak Bioorg. Med. Chem. Lett. 20 2010 3244
9. A. Fajdetić, H. Čipčić Paljetak, V. Šunjić, G. Lazarevski, J. Berge, A. Hutinec, M. Djerek, V. Štimac, S. Mutak, M. Dumić, D. Andreotti, D.J. Holmes, V. Eraković Haber, S. Alihodzic, and R. Spaventi Bioorg. Med. Chem. 18 2010 6559
10. I. Palej Jakopović, G. Kragol, A.K. Forrest, V.C.S. Frydrych, V. Štimac, S. Kapić, H. Čipčić Paljetak, D. Jelić, D.J. Holmes, D.M.B. Hickey, D. Verbanac, V. Eraković Haber, and S. Alihodžić Bioorg. Med. Chem. 18 2010 6578
11. S. Kapić, H. Čipčić Paljetak, S. Alihodžić, R. Antolović, V. Eraković Haber, D.J. Holmes, P.J. Broskey, and E. Hunt Bioorg. Med. Chem. 18 2010 6569
12. H. Sano, T. Sunazuka, H. Tanaka, K. Yamashita, R. Okachi, and S. Omura J. Antibiot. 37 1984 750
13. K. Sonogashira J. Organomet. Chem. 633 2002 46
14. R. Rossi, A. Carpita, and F. Bellina Org. Prep. Proceed. Int. 27 1995 129
15. V. Ceccheti, S. Clementi, G. Cruciani, A. Fravolini, P.G. Pagella, A. Savino, and O.J. Tabarrini Med. Chem. 38 1995 973
16. Hooper, D. C.; Rubinstein, E. Quinolone Antimicrobial Agents, 3rd ed.; ASM Press; American Society for Microbiology, 1752N Street NW, Washington, DC, 2003; pp 3, 2036.
17. J. Ellis, E. Gellert, and J. Robson Aust. J. Chem. 26 1973 907
18. W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley & Sons Inc. p 518
19. Derek, M.; Kidemet, D.; Leljak, M. WO 2004/106353 (12.09.2004.).
20. Derek, M.; Kidemet, D.; Lazarevski, G.; Leljak, M. WO 2004/106354 (12.09.2004.).
21. Alihodžić, S.; Andreotti, D.; Berdik, A.; Bientinesi, I.; Biondi, S.; Ciraco, M.; Damiani, F.; erek, M.; Dumić, M.; Eraković, V.; Hutinec, A.; Lazarevski, G.; Lociuro, S.; Maršić, N.; Marušić Ištuk, Z.; Mutak, S.; Paio, A.; Pavlović, D.; Quaglia, A.; Schoenfeld, W.; Štimac, V.; Tibasco, J. WO 03/042228 (22.05.2003).
22. Berge, J.; Forrest, A.; Jarvest, R. WO 2004 101589.
23. Y. Huang, and X. Lu Tetrahedron Lett. 29 1988 5663
24. F. Buono, and A. Tenaglia J. Org. Chem. 65 2000 3869
25. D.J. Plata, M.R. Leanna, M. Rasmussen, M.A. McLaughlin, S.L. Condon, F.A.J. Kerdesky, S.A. King, M.J. Peterson, E.J. Stoner, and S.J. Wittenberger Tetrahedron 60 2004 10171
26. A.R. Haight, E.J. Stoner, M.J. Peterson, and V.K. Grover J. Org. Chem. 68 2003 8092
27. R. Lakhmiri, P. Lhoste, and D. Sinou Tetrahedron Lett. 30 1989 4669
28. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
29. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
30. G. Lazarevski, M. Vinkovic, G. Kobrehel, and S. Djokic Tetrahedron 49 1993 721
31. W. Steinmetz, R. Bersch, J. Towson, and D. Pesiri J. Med. Chem. 35 1992 4842
32. B.M. Trost, and D. van Vranken Chem. Rev. 96 1996 395
33. B.M. Trost, M.R. Machacek, and A. Aponick Acc. Chem. Res. 39 2006 747
34. A. Heumann, and M. Reglier Tetrahedon 51 1995 975
35. Clinical Laboratory Standard Institute CLSI. 2005. Performance Standards for Antimicrobial Susceptibility Testing: 15th Informational Supplement M100-S15. Clinical Laboratory Standards Institute, Wayne, PA, 2005.
36. V.D. Shortridge, P. Zhong, Z. Cao, J.M. Beyer, L.S. Almer, N.C. Ramer, S.Z. Doktor, and R.K. Flamm Antimicrob. Agents Chemother. 46 2002 783
37. D. Verbanac, D. Jelić, V. Stepanić, I. Tatić, D. Žiher, and S. Koštrun Croat. Chem. Acta 78 2005 133