beta-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogues, unusually specific immunosuppressive agents.
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.
D000818:Animals; D000917:Antibody Formation / Q000187:drug effects; D000998:Antiviral Agents / Q000138:chemical synthesis; D003601:Cytotoxicity Tests, Immunologic; D004912:Erythrocytes / Q000276:immunology; D006462:Hemolytic Plaque Technique; D006564:Herpesviridae / Q000187:drug effects; D007109:Immunity / Q000187:drug effects; D007111:Immunity, Cellular / Q000187:drug effects; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D066298:In Vitro Techniques; D007519:Isoantigens; D051379:Mice; D009712:Nucleotides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D013154:Spleen / Q000276:immunology; D013601:T-Lymphocytes / Q000187:drug effects / Q000276:immunology; D014227:Triazines / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D007166:Immunosuppressive Agents; D007519:Isoantigens; D009712:Nucleotides, Cyclic; D014227:Triazines