Azidamfenicol is a semi-synthetic chloramphenicol in which the nitro moiety is replaced with a methylsulphone and the dichloroacetamide is replaced with azidoacetamide, first synthesised at Bayer in 1959. Azidamfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Azidamfenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Azidamfenicol has received little research attention with only a few literature citations.
ChEBI: Azidamfenicol is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
21.2 g of D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol are stirred
with 10 g of azidoacetonitrile (B.P. 68°C/25 mm) in a mixture of 125 ml of
methanol and 125 ml of water at 30-40°C for a few days. The mixture is
filtered off from a little undissolved base and the solvent is distilled in vacuo.
The residue is treated with a little normal hydrochloric acid until acid to Congo
red and extracted with ethylacetate. By evaporating the solvent and
recrystallizing the residue from ethylene chloride is obtained D-(-)-threo-1-pnitrophenyl-
2-azidoacetylamino-propane-1,3-diol, M.P. 107°C.
