10-Formyl-5,8,10-trideazafolic acid (10-formyl-TDAF): A potent inhibitor of glycinamide ribonucleotide transformylase

Dale L. Boger, Nancy Ellen Haynes, Paul A. Kitos, Mark S. Warren, Joseph Ramcharan, Ariane E. Marolewski, Stephen J. Benkovic

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43 Scopus citations


The synthesis of 10-formyl-5,8,10-trideazafolic acid (3) as a potential inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) is reported. The target compound was prepared by a convergent synthesis utilizing the alkylation of hydrazone 5 with benzylic bromide 6 to construct the core heterocycle 7. The aldehyde 3 and related agents were evaluated as inhibitors of purN GAR Tfase and avian AICAR Tfase. Compound 3 exhibited potent inhibition of GAR Tfase with a K(i) of 0.26 ± 0.05 μM. In contrast, 3 exhibited more moderate inhibition of aminoimidazole carboxamide ribonucleotide transformylase (AICAR Tfase), with K(i) of 7.6 ± 1.5 μM.

Original languageEnglish (US)
Pages (from-to)1817-1830
Number of pages14
JournalBioorganic and Medicinal Chemistry
Issue number9
StatePublished - Sep 1997

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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