头孢氮氟

化合物

头孢氮氟INN:Cefazaflur)是第一代头孢菌素类抗生素。

头孢氮氟
临床资料
ATC码
  • 未分配
识别信息
  • (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
CAS号58665-96-6
52123-49-6  checkY
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
化学信息
化学式C13H13F3N6O4S3
摩尔质量470.46 g·mol−1
3D模型(JSmol英语JSmol
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSC(F)(F)F)CSc3nnnn3C)C(=O)O
  • 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

合成

头孢氮氟在这组类似物中脱颖而出,因为它缺乏芳酰胺C-7侧链(另一个例子参见头孢乙腈)。

 
头孢氮氟合成:[1]

头孢氮氟是通过3-(1-甲基-1H-四唑-5-基硫代亚甲基)-7-氨基-头孢烯-4-甲酸(1)与三氟甲硫基乙酰氯(2)反应合成的。

参考资料

  1. ^ DeMarinis RM, Boehm JC, Dunn GL, Hoover JR, Uri JV, Guarini JR, et al. 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. January 1977, 20 (1): 30–5. PMID 319233. doi:10.1021/jm00211a006.