Preparation and antitumor activities of 5-azaheterocyclic-2,4-diaminopyrimidines

H. Wang*, L. M. Werbel

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review


A series of 6-alkyluracils 1-10 with azaheterocyclic substitutions at C-5 position were synthesized by condensation of 6-alkyl-5-bromouracils with relevant azaheterocycles with the catalysis of potassium fluoride. Chlorination and subsequent amination of the uracils afforded 6-alkyl-5-(1-azaheterocyclic)-2,4-diaminopyrimidines 21-30. Most of the diaminopyrimidines exhibited moderate to high cytotoxicity on L1210 murine leukemia cell line with 5-(azabicyclo[3,2,2]non-3-yl)-6-ethyl-2,4-diaminopyrimidine (30) the most active with ID50 of 2.6 x 10-9 M. This compound is unfortunately devoid of in vivo antitumor activity on mice bearing lymphocytic leukemia P388. Most of the diaminopyrimidines except compounds 22 and 24 exhibited moderate cytotoxic activity against human colon adenocarcinoma cell line with ID50's between 10-6 to 10-8 M.

Original languageEnglish
Pages (from-to)521-529
Number of pages9
JournalChinese Pharmaceutical Journal
Issue number6
StatePublished - 1995
Externally publishedYes


  • 5-azaheterocyclic-2,4-diaminopyrimidines
  • antifolates
  • antitumor activity


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