Lysine and Ornithine Analogues of Methotrexate as Inhibitors of Dihydrofolate Reductase

Robert J. Kempton, Angelique M. Black, Gregory M. Anstead, A. Ashok Kumar, Dale T. Blankenship, James H. Freisheim

Research output: Contribution to journalComment/debatepeer-review

24 Scopus citations

Abstract

The ornithine (6a) and lysine (6b) analogues of methotrexate (1) have been synthesized via condensation of 4-amino-4-deoxy-N10-methylpteroic acid (2) with Nδ-carbobenzoxy-l-ornithine tert-butyl ester (3a) and Nϵ-carbobenzoxy-l-lysine tert-butyl ester (3b), respectively. Removal of the protecting groups gave 6a and 6b. Compounds 6a and 6b and their precursor Cbz acids (5a and 5b) show significant inhibition of dihydrofolate reductase.

Original languageEnglish (US)
Pages (from-to)475-477
Number of pages3
JournalJournal of Medicinal Chemistry
Volume25
Issue number4
DOIs
StatePublished - Jan 1 1982
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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