Arclofenin

Originator

Arclofenin,ZYF Pharm Chemical

Uses

Diagnostic aid (hepatic function determination).

Uses

Arclofenin is derived from Nitrilotriacetic Acid (N490175), which is a chelating agent which forms coordination compound with metal ions. Nitrilotriacetic acid is used in complexometric titrations and as well as for protein isolation and purification in the His-tag method.

Definition

ChEBI: Arclofenin is a member of benzophenones.

Manufacturing Process

A round bottom flask is charged with dimethylformamide 72.0 g, acetic anhydride 25.0 g, pyridine 2.0 g, and nitrilotriacetic acid (NTA) 38.2 g and the suspension is nitrogen purged for several minutes. The flask is stoppered and the mixture is stirred at room temperature for 3 days. A small amount of unreacted NTA is filtered out. The bulk of the solvent 79 ml is removed in vacuo at a bath temperature of 60°-70°C. The resulting viscous solution is twice roto-vacued after two successive additions of 40 ml dimethylformamide. So the 2,6-diketo-N-carboxymethyl morpholine (NTA anhydride) is prepiared.
To the viscous solution of NTA anhydride is added 300 ml toluene. The mixture is stirred at room temperature until uniform. Then 46.3 g of 2-amino- 5-chlorobenzophenone dissolved in 300 ml toluene is added to the stirred solution of NTA anhydride and heated at 90°-100°C for 1 h. After cooling, the reaction mixture is flashed to dryness. The residue is taken up in 400 ml of 1N sodium hydroxide and filtered. The filtrate is extracted with chloroform, ether and charcoaled. The charcoal is removed by filtration. The product is precipitated from the filtrate by the careful addition of 6 N HCl. The precipitate is removed by filtration to give the N-[N'-(2-benzoyl-4- chlorophenyl)carbamoylmethyl]iminodiacetic acid, melting point 180°-186°C (dec., recrystallized from hot methanol/water).

Therapeutic Function

Diagnostic aid

Raw materials

Preparation Products