Cyclic homopentapeptides 3. Synthetic modifications to the capreomycins and tuberactinomycins: Compounds with activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 9, 1997, Pages 1149-1152

  Linde II, R G ^a   Birsner, N C ^a   Chandrasekaran, R Y ^a   Clancy, J ^a   Howe, R J ^a   Lyssikatos, J P ^a   MacLelland, C P ^a   Magee, T V ^a   Petitpas, J W ^a   Rainville, J P ^a   Su, W G ^a   Vu, C B ^a   Whipple, D A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CAPREOMYCIN; CIPROFLOXACIN; METICILLIN; PENTAPEPTIDE; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG RESISTANCE; DRUG SYNTHESIS; ENTEROCOCCUS; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION;

EID: 18344411249     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00188-1     Document Type: Article

References (10)

1. Dirlam, J. P.; Belton, A. M.; Birsner, N. C; Brooks, R. R.; Chang, S.-P.; Chandrasekaran, R. Y.; Clancy, J.; Cronin, B. J.; Dirlam, B. P.; Finegan, S. M.; Froshauer, S. A.; Girard, A. E.; Hayashi, S. F.; Howe, R. J.; Kane, J. C.; Kaufman, S. A.; Kolosko, N. L.; LeMay, M. A.; Linde II, R. G.; Lyssikatos, J. P.; MacLelland, C. P.; Magee, T. V.; Miller, S. A.; Minich, M. L.; Perry, D. A.; Petitpas, J. W.; Rainville, J. P.; Reese, C. P.; Su, W.-G.; Whipple, D. A.; Yang B. V. Bioorg. Med. Chem. Lett. first paper in this series.
2. The highly charged, highly water soluble cyclic homopentapeptide capreomycins and tuberactinomycins are not soluble in most organic solvents other than methanol or DMF. Most of the chemistry, therefore, was carried out in water or with water as a co-solvent.
3. This result plus the results described in the preceding paper suggested that incorporation of a lipophilic group at any position might lead to improved activity. Lyssikatos, J. Chang, S.-P.; Clancy, J.; Dirlam, J. P.; Finegan, S. M.; Girard, A. E.; Hayashi, S. F.; Larson, D. P.; Lee, A.; Linde II, R. G.; MacLelland, C. P.; Petitpas, J. W.; Seibel, S.; Vu, C. B. Bioorg. Med. Chem. Lett. preceding paper
4. Wakamiya, T.; Shiba, T. J. Antibiot. 1983, 36, 197.
5. (a) Wakamiya, T.; Teshima, T.; Sakakibara, H.; Fukukawa. K.; Shiba, T. Bull. Chem. Soc. Japan 1977, 50, 1984.
6. (b) Yamada, T.; Teshima, T.; Shiba, T. Antimicrob. Agents Chemother. 1981, 20, 834
7. (a) Takahashi, S.: Yanagida, Y. European Patent Application 0 430 234 A2, Kanegafuchi Chemical Industry Co., Ltd.
8. (b) Kawaguchi, H.; Naito, T.; Nakagawa, S.; Fujisawa, K.J. Antibiot. 1972, 25, 695.
9. The in vivo efficacy of representative cyclic homopentapeptides will be described in a subsequent report.
10. MIC=minimal inhibitory concentration as determined by NCCLS document 197-A3, December, 1993. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. 3rd Edition.