Chang C T, Edwards M W, Torrence P F, Mertes M P
J Med Chem. 1979 Sep;22(9):1137-9. doi: 10.1021/jm00195a028.
The 5'-phosphate (1) of the antiviral nucleoside 5-cyano-2'-deoxyuridine was synthesized and evaluated for inhibition of thymidylate synthetase purified from methotrexate-resistant Lactobacillus casei. Compound 1 was a potent competitive inhibitor with a K1 of 0.55 microns. Irreversible enzyme inhibition by this compound could not be detected.