Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents. 1. Identification of leads and importance of the tropone substitution pattern

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 9, 1996, Pages 1003-1008

  Barbachyn, Michael R ^a   Toops, Dana S ^a   Ulanowicz, Debra A ^a   Grega, Kevin C ^a   Brickner, Steven J ^a   Ford, Charles W ^a   Zurenko, Gary E ^a   Hamel, Judith C ^a   Schaadt, Ronda D ^a   Stapert, Douglas ^a   Yagi, Betty H ^a   Buysse, Jerry M ^a   Demyan, William F ^a   Kilburn, James O ^b   Glickman, Suzanne E ^b  

^a PFIZER INC   (United States)

^b CENTERS FOR DISEASE CONTROL AND PREVENTION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; 3 [4 (1 OXO 2 PROPARGYLAMINO 6 TROPONYL)PHENYL] 2 OXAZOLIDINONE; 3 [4 (2 METHYLAMINO 1 OXO 6 TROPONYL)PHENYL] 2 OXAZOLIDINONE; ANTIINFECTIVE AGENT; N [[3 (4 ACETYLPHENYL) 2 OXO 5 OXAZOLIDINYL]METHYL]ACETAMIDE; TROPONE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL INFECTION; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM POSITIVE BACTERIUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; ORAL DRUG ADMINISTRATION; STEREOCHEMISTRY;

EID: 0029995925     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00154-0     Document Type: Article

References (20)

1. Tomasz, A. New Eng. J. Med. 1994, 330, 1247.
2. Spera, R. V., Jr.; Farber, B. F. Drugs 1994, 48, 678.
3. Brumfitt, W.; Hamilton-Miller, J. M. T. Drugs Exptl. Clin. Res. 1994, 20, 215.
4. Appelbaum, P. C. Clin. Infect. Dis. 1992, 15, 77.
5. Gregory, W. A.; Brittelli, D. R.; Wang, C.-L. J.; Wuonola, M. A.; McRipley, R. J.; Eustice, D. C.; Eberly, V. S.; Bartholomew, P. T.; Slee, A. M.; Forbes, M. J. Med. Chem. 1989, 32, 1673.
6. Slee, A. M.; Wuonola, M. A.; McRipley, R. J.; Zajac, I.; Zawada, M. J.; Bartholomew, P. T.; Gregory, W. A.; Forbes, M. Antimicrob. Agents. Chemother. 1987, 31, 1791.
7. Ashtekar, D. R.; Costa-Periera, R.; Shrinivasan, T.; Iyyer, R.; Vishvanathan, N.; Rittel, W. Diagn. Microbiol. Infect. Dis. 1991, 14, 465.
8. Eustice, D. C.; Feldman, P. A.; Zajac, I.; Slee, A. M. Antimicrob. Agents. Chemother. 1988, 32, 1218.
9. Pharmcast-International 1995, February, 7-1-487.
10. Unpublished results of R. C. Piper, T. F. Platte, J. R. Palmer, Pharmacia & Upjohn.
11. Brumfitt, W.; Hamilton-Miller, J. M. T. Diagn. Microbiol. Infect. Dis. 1992, 15, 621.
12. A preliminary account of this work has been presented: Abstracts of Papers, 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, September, 1995; American Society for Microbiology: Washington, DC, 1995; Abstract No. F206.
13. Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543. Amon, C. M.; Banwell, M. G.; Gravatt, G. L. J. Org. Chem. 1987, 52, 4851. Banwell, M. G.; Lambert, J. N.; Reum, M. E.; Onrust, R. Org. Prep. Proc. Intl. 1988, 393.
14. Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543. Amon, C. M.; Banwell, M. G.; Gravatt, G. L. J. Org. Chem. 1987, 52, 4851. Banwell, M. G.; Lambert, J. N.; Reum, M. E.; Onrust, R. Org. Prep. Proc. Intl. 1988, 393.
15. Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 26, 4543. Amon, C. M.; Banwell, M. G.; Gravatt, G. L. J. Org. Chem. 1987, 52, 4851. Banwell, M. G.; Lambert, J. N.; Reum, M. E.; Onrust, R. Org. Prep. Proc. Intl. 1988, 393.
16. 1H NMR, low and high resolution MS) were obtained for all new compounds.
17. Wulff, W. D.; Peterson, G. A.; Bauta, W. E.; Chan, K.-S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 279.
18. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
19. Intermediate (±)-6 was prepared from aniline via a procedure employing an iodocyclocarbamation reaction as its key step: Grega, K. C.; Barbachyn, M. R.; Brickner, S. J.; Mizsak, S. A. J. Org. Chem. 1995, 60, 5255. For the synthesis of (S) see: Gregory, W. A.; Brittelli, D. R.; Wang, C.-L. J.; Kezar, H. S., III; Carlson, R. K.; Park, C-H.; Corless, P. F.; Miller, S. J.; Rajagopalan, P.; Wuonola, M. A.; McRipley, R. J.; Eberly, V. S.; Slee, A. M.; Forbes, M. J. Med. Chem. 1990, 33, 2569.
20. Intermediate (±)-6 was prepared from aniline via a procedure employing an iodocyclocarbamation reaction as its key step: Grega, K. C.; Barbachyn, M. R.; Brickner, S. J.; Mizsak, S. A. J. Org. Chem. 1995, 60, 5255. For the synthesis of (S) see: Gregory, W. A.; Brittelli, D. R.; Wang, C.-L. J.; Kezar, H. S., III; Carlson, R. K.; Park, C-H.; Corless, P. F.; Miller, S. J.; Rajagopalan, P.; Wuonola, M. A.; McRipley, R. J.; Eberly, V. S.; Slee, A. M.; Forbes, M. J. Med. Chem. 1990, 33, 2569.