26973-24-0

Ceftezole,Arocor Holdings Inc.

Ceftezole is a β-lactam, cephem antibiotic. It also exhibits potent α-glucosidase inhibitory activity and antidiabetic effect in streptozotocin-induced mouse.

ChEBI: Ceftezole is a first-generation cephalosporin antibiotic having (1,3,4-thiadiazol-2-ylsulfanyl)methyl and [2-(1H-tetrazol-1-yl)acetamido side groups located at positions 3 and 7 respectively. It is a cephalosporin and a member of thiadiazoles.

To a solution of 1 equivalent (eq.) of 1H-tetrazole-1-acetic acid and 1 eq. of triethylamine in 20 ml of tetrahydrofuran cooled to -20°C was added 1 eq. of pivaloyl chloride. After thirty-minute stirring of the mixture 20 ml of a chloroform solution containing 1 eq. of and 1 eq. of triethylamine was poured into the solution cooled at -10°C during a period of 30 minutes. The resulting mixed solution was stirred for 30 minutes at the same temperature, for 1 hour in an ice-water mixture and for 3 hours at room temperature. Removal of a solvent from the reaction mixture afforded an oily residue, which was dissolved into 15 ml of 10% sodium bicarbonate aqueous solution. The resulting aqueous layer was adjusted to pH 1.0-2.0 with 10% hydrochloric acid, washed with ether and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure leaving a residue which was triturated with ethyl acetate to obtain 3- acetoxymethyl-8-oxo-7-(2-tetrazol-1-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
A solution of 1 eq. of sodium salt of 3-acetoxymethyl-8-oxo-7-(2-tetrazol-1- acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (it may be prepared with equivalent of sodium bicarbonate and above named acid) and 1 eq. of [1.3.4]-thiadiazole-2-thiol in 20 ml of phosphate buffer (pH 6.4) was stirred for 5.5 hours at 60°C. The reaction mixture was adjusted to pH 2.0 with 5% hydrochloric acid and treated with ethyl acetate to form a title compound - ceftezole.

Antibiotic