Cefazaflur
Cephalosporin antibiotic
- none
- (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
- 58665-96-6
- Sodium: 52123-49-6 Y
- 40240
- 36777
- 97I0692RNT
- Sodium: 8NJ5RWV39D Y
- D03422 Y
- ChEMBL2104456
- DTXSID30207368
- Interactive image
- 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
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 is synthesized by reaction of 3-(1-methyl-1H-tetrazol-5-ylthiomethylene)-7-amino-cephem-4-carboxylic acid (1) with trifluoromethylthioacetyl chloride (2).
References
- ^ DeMarinis RM, Boehm JC, Dunn GL, Hoover JR, Uri JV, Guarini JR, et al. (January 1977). "Semisynthetic cephalosporins. Synthesis and structure-activity relationships of analogues 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.
- v
- t
- e