Effect of aryl ring fluorination on the antibacterial properties of C4 aryl-substituted N-methylthio β-lactams

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 8, 2003, Pages 1859-1863

  Long, Timothy E ^a   Turos, Edward ^a   Konaklieva, Monika I ^b   Blum, Allison L ^b   Amry, Amal ^b   Baker, Ejae A ^b   Suwandi, Lita S ^b   McCain, Melodie D ^b   Rahman, Miti F ^b   Dickey, Sonja ^a   Lim, Daniel V ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b AMERICAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXY 1 (METHYLTHIO) 4 (2,3,4 TRIFLUOROPHENYL)AZETIDIN 2 ONE; 3 METHOXY 1 (METHYLTHIO) 4 (2,3,5 TRIFLUOROPHENYL)AZETIDIN 2 ONE; 3 METHOXY 1 (METHYLTHIO) 4 (2,3,6 TRIFLUOROPHENYL)AZETIDIN 2 ONE; 3 METHOXY 1 (METHYLTHIO) 4 (2,4,5 TRIFLUOROPHENYL)AZETIDIN 2 ONE; 3 METHOXY 1 (METHYLTHIO) 4 (3,4,5 TRIFLUOROPHENYL)AZETIDIN 2 ONE; 3 METHOXY 1 (METHYLTHIO) 4 (PENTAFLUOROPHENYL)AZETIDIN 2 ONE; 4 (2 FLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (2,3 DIFLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (2,5 DIFLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (2,6 DIFLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (3 FLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (3,4 DIFLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (3,5 DIFLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; 4 (4 FLUOROPHENYL) 3 METHOXY 1 (METHYLTHIO)AZETIDIN 2 ONE; ANTIINFECTIVE AGENT; BETA LACTAM ANTIBIOTIC; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG EFFECT; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME BINDING; FLUORINATION; HYDROPHOBICITY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 12244284654     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00037-3     Document Type: Article

References (9)

1. Turos E., Konaklieva M.I., Ren R.X.F., Shi H., Gonzalez J., Dickey S., Lim D. Tetrahedron. 56:2000;5571.
2. Turos E., Long T.E., Konaklieva M.I., Coates C., Shim J.-Y., Dickey S., Lim D.V., Cannons A. Bioorg. Med. Chem. Lett. 12:2002;2229.
3. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982; Vols. 1-3.
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5. (b) Park C.-H., Brittelli D.R., Wang C.L.-J., March F.D., Gregory W.A., Wuonola M.A., McRipley R.J., Eberly V.S., Slee A.M., Forbes M. J. Med. Chem. 35:1992;1156.
6. Ren X.-F., Konaklieva M.I., Shi H., Dickey S., Lim D.V., Gonzalez J.; Turos, E. J. Org. Chem. 63:1998;8898.
7. cis-Disubstituted β-lactams typically display a coupling constant of 4.8-6. 0 Hz for the two vicinal protons on the ring, while for the trans isomer, the value is normally in the range of 1-3 Hz.
8. 4 saturated side-chain analogues. See Coates C., Long T.E., Turos E., Dickey S., Lim D.V. Bioorg. Med. Chem. 11:2003;193.
9. NCCLS (National Committee for Clinical Laboratory Standards) Methods for Dilution of Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. NCCLS Document M7-A4, Vol. 17, No. 2, 1997.