Synthesis and Biological Properties of a Novel Cephalosporin FR86521 Having Potent Activity Against Methicillin-resistant Staphylococcus aureus (MRSA)

Recently, we introduced cefoselis (CFSL), which shows potent broad-spectrum activity against both Gram-positive bacteria, including MRSA, and Gram-negative bacteria, including P. aeruginosa. CFSL has a 7 beta -[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] side chain. We have focused recent e...

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Bibliographic Details
Published inJournal of antibiotics Vol. 52; no. 12; pp. 1152 - 1155
Main Authors KISHI, KOHEI, OHKI, HIDENORI, OKUDA, SHINYA, KAWABATA, KOHJI, SAKANE, KAZUO, MATSUMOTO, YOSHIMI, MATSUMOTO, SATORU, TAWARA, SHUICHI
Format Journal Article
LanguageEnglish
Published TOKYO JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1999
JAPAN ANTIBIOT RES ASSN
Japan Antibiotics Research Association
Subjects
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Biotechnology & Applied Microbiology
cefoselis
Cephalosporins - chemical synthesis
Cephalosporins - pharmacology
General pharmacology
Immunology
Life Sciences & Biomedicine
Medical sciences
Methicillin Resistance
Microbiology
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Science & Technology
Staphylococcus aureus
Staphylococcus aureus - drug effects
ANTIBACTERIAL ACTIVITY
FK037
SERIES
Pseudomonadales
Meticillin
Penicillin derivatives
Structure activity relation
Bacteria
Micrococcales
Pseudomonadaceae
Pseudomonas aeruginosa
Micrococcaceae
Chemical synthesis
Staphylococcus aureus
β-Lactams
Rodentia
In vitro
Biological activity
Infection
Resistance
In vivo
Vertebrata
Antibiotic
Cephalosporin derivatives
Mammalia
Mouse
Animal
Minimum inhibitory concentration
Bacteriosis
Antibacterial agent
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Summary:Recently, we introduced cefoselis (CFSL), which shows potent broad-spectrum activity against both Gram-positive bacteria, including MRSA, and Gram-negative bacteria, including P. aeruginosa. CFSL has a 7 beta -[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] side chain. We have focused recent efforts on synthesizing novel cephalosporins superior to CFSL in antibacterial activity against both MRSA and P. aeruginosa, and as a result, we have discovered FR86521 (1) having a 7 beta -[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido] side chain. In this paper, we report the synthesis, and in vitro with 3 N hydrochloric acid in ethanol-acetone to produce FR86521 in 54.8% yield. The structure of FR86521 was confirmed by IR, super(1)H NMR, MS and elemental analysis.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.52.1152