Cefazaflur

Cefazaflur

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
KEGG	D03422
ChEMBL	CHEMBL2104456
Chemical data
Formula	C13H13F3N6O4S3
Molar mass	470.470 g/mol
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSC(F)(F)F)CSc3nnnn3C)C(=O)O
InChI InChI=1S/C13H13F3N6O4S3/c1-21-12(18-19-20-21)28-3-5-2-27-10-7(9(24)22(10)8(5)11(25)26)17-6(23)4-29-13(14,15)16/h7,10H,2-4H2,1H3,(H,17,23)(H,25,26)/t7-,10-/m1/s1 Key:HGXLJRWXCXSEJO-GMSGAONNSA-N
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Cefazaflur (INN) is a first-generation cephalosporin antibiotic.

Synthesis

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

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.