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, Roland K. Robins, Tasneem A. Khwaja

Research output: Contribution to journalArticle

10 Citations (Scopus)

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
Pages (from-to)514-518
Number of pages5
JournalJournal of Medicinal Chemistry
Volume22
Issue number5
StatePublished - Dec 1 1979
Externally publishedYes

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Antiviral Agents
Phosphates
Derivatives
Flucytosine
Viruses
Bearings (structural)
Leukemia L1210
DNA Viruses
Cytarabine
Human Herpesvirus 1
DNA

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Mian, A. M., Long, R. A., Allen, L. B., Sidwell, R. W., Robins, R. K., & Khwaja, T. A. (1979). Synthesis and antitumor and antiviral activities of 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-iminopyrimidine and its derivatives. Journal of Medicinal Chemistry, 22(5), 514-518.

Synthesis and antitumor and antiviral activities of 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-iminopyrimidine and its derivatives. / Mian, A. Mohsin; Long, Robert A.; Allen, Lois B.; Sidwell, Robert W.; Robins, Roland K.; Khwaja, Tasneem A.

In: Journal of Medicinal Chemistry, Vol. 22, No. 5, 01.12.1979, p. 514-518.

Research output: Contribution to journalArticle

Mian, AM, Long, RA, Allen, LB, Sidwell, RW, Robins, RK & Khwaja, TA 1979, 'Synthesis and antitumor and antiviral activities of 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-iminopyrimidine and its derivatives', Journal of Medicinal Chemistry, vol. 22, no. 5, pp. 514-518.
Mian, A. Mohsin ; Long, Robert A. ; Allen, Lois B. ; Sidwell, Robert W. ; Robins, Roland K. ; Khwaja, Tasneem A. / Synthesis and antitumor and antiviral activities of 1-β-D-arabinofuranosyl-2-amino-1,4(2H)-iminopyrimidine and its derivatives. In: Journal of Medicinal Chemistry. 1979 ; Vol. 22, No. 5. pp. 514-518.
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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.",
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AU - Robins, Roland K.

AU - Khwaja, Tasneem A.

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