.beta.-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogs, unusually specific immunosuppressive agents

Journal of Medicinal Chemistry
1978.0

Abstract

Sequential treatment of the protected beta-D-arabinofuran[1',2':4,5]-2-aminooxazoline (2) with methyl isocyanate and diimidazole carbonyl afforded the 2,2'-anhydro-beta-D-arabinofuranosyl nucleoside, 6. Deprotection and hydrolysis yielded the corresponding arabinoside. Although the anhydronucleoside exhibited in vitro antiviral activity against herpes simplex type 1, it exacerbated the infection in vivo. Further examination uncovered an in vitro inhibition of the induction of a cell-mediated immune response without cytotoxicity.

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