CAS 6629-04-5: Ethyl N-(2-cyanoacetyl)carbamate

Ethyl N-(2-cyanoacetyl)carbamate

Applications N-Cyanoacetylurethane-13C3,15N2 is an intermediate for the synthesis of Diclazuril-13C3,15N2 (D436202), which is the labelled analogue of Diclazuril (D436200). Diclazuril is a nucleotide analogue with broad-spectrum anticoccidial activity and a coccidiostat. References Maes, L., et al.: J. Parasitol., 74, 931 (1988)

N-Cyanoacetylurethane is a heterocyclic compound that is an isomer of urethane. The synthesis of the molecule starts with the reaction of ethyl orthoformate and paraformaldehyde to form an amide. The amide is then reacted with chloroacetic acid to form the desired product. N-Cyanoacetylurethane has been shown to be an antifungal agent, inhibiting the growth of yeast cells by disrupting their cell membranes. This drug also has a reductive elimination when in acidic environments, leading to its decomposition into carbon dioxide and ammonia which can be toxic if inhaled.

Applications N-Cyanoacetylurethane is used in the synthesis of inhibitors targetting the PDZ domain of PICK1, which is a potential target for brain ischemia, pain and addiction illnesses. Also it is used in the synthesis of cathespin K inhibitors. References Bach, A. et al.: Org. Biomol. Chem., 8, 4281 (2010); Rankovic, Z. et al.: Bioorg. Med. Chem. Lett., 20, 1488 (2010);