Cefazaflur

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Cefazaflur
Cefazaflur.png
Systematic (IUPAC) name
(6R,7R)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-([2-(trifluoromethylsulfanyl)acetyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS Number 52123-49-6
ATC code none
PubChem CID 40240
ChemSpider 36777
UNII 97I0692RNT YesY
KEGG D03422 YesY
ChEMBL CHEMBL2104456
Chemical data
Formula C13H13F3N6O4S3
Molar mass 470.470 g/mol
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Cefazaflur (INN) is a first-generation cephalosporin antibiotic.

Synthesis[edit]

Cefazaflur stands out among this group of analogues because it lacks an arylamide C-7 side chain (see cephacetrile for another example).

Cefazaflur synthesis:[1]

Cefazaflur is synthesized by reaction of 3-(1-methyl-1H-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid (1) with trifluoromethylthioacetyl chloride (2).

References[edit]

  1. ^ Demarinis, R. M.; Boehm, J. C.; Dunn, G. L.; Hoover, J. R. E.; Uri, J. V.; Guarini, J. R.; Phillips, L.; Actor, P.; Weisbach, J. A. (1977). "Semisynthetic cephalosporins. Synthesis and structure-activity relations of analogs with 7-acyl groups derived from 2-(cyanomethylthio)acetic acid or 2-[(2,2,2-trifluoroethyl)thio]acetic acid and their sulfoxides and sulfones". Journal of Medicinal Chemistry. 20 (1): 30–5. doi:10.1021/jm00211a006. PMID 319233.