Synthesis and Antitumor and Antiviral Activities of 1-β-D-Arabinofuranosyl-2-amino-1, 4(2H)-iminopyrimidine, and Its Derivatives

A. Mohsin Mian, Robert A. Long, Lois B. Allen, Robert W. Sidwell, Tasneem A. Khwaja, Roland K. Robins

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

1-β-D-Arabinofuranosyl-2-amino-1,4(2H)-imino-5-fluoropyrirnidine (10), 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-imino-5-fluoropyrimidine 3′-phosphate (9), and 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-imino-5-chloropyrimidine (11) have been synthesized from 2,2′-anhydro-1-β-D-arabinofuranosyl-5-fluorocytosine (5), 2,2′-anhydro-1-β-D-arabinofuranosyl-5-fluorocytosine 3′-phosphate (4), and 2,2′-anhydro-1-β-D-arabinofuranosyl-5-chlorocytosine (6), respectively. 2,2′-Anhydro-1-β-D-arabinofuranosylcytosine 3′-phosphate (7), 1-β-D-arabinofuranosyl-2-amino-1,4-(2H)-iminopyrimidine (13), 1-β-D-arabinofuranosyl-2-amino-1,3(2H)-iminopyrimidine 3′-phosphate (12), and compounds 4, 5, and 9 showed significant in vitro activity against a number of DNA viruses. Compounds 7 and 12 were also effective in vivo against type 1 herpes simplex virus. Compounds 7, 12, and 13 were extremely effective in the treatment of mice bearing leukemia L1210.

Original languageEnglish (US)
Pages (from-to)514-518
Number of pages5
JournalJournal of Medicinal Chemistry
Volume22
Issue number5
DOIs
StatePublished - Feb 1 1979

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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