Synthesis of 8-(3'-deoxy-alpha-D-threo-pentofuranosyl) adenine and 9-(3'-deoxy-alpha-D-threo-pentofuranosyl) adenine.
3-Deoxy-2,5-di-O-p-nitrobenzoyl-alpha-D-threo-entofuranosyl bromide (1) reacted with mercuric cyanide to give 2,5-anhydro-4-deoxy-D-lyxo-hexononitrile (2) which upon acid hydrolysis of the CN group gave acid 3. Saponification of the protecting groups gave 2,5-anhydro-4-deoxy-D-lyxo-hexonic acid (4) which reacted with 4,5,6-triaminopyrimidine forming an amide (5) that was pyrolized to give 8-(3'-deoxy-alpha-D-threo-pentofuranosyl) adenine (6). Reaction of bromide 1 with 6-(benzamido) chloromercuriopurine followed by saponification yielded 9-(3'-deoxy-alpha-D-threo-pentofuranosyl)adenine(8). 8-(beta-D-Ribofuranosyl)adenine, 8-(beta-D-arabinofuranosyl)adenine, and 8-(3'-deoxy-beta-D-erythro-pentofuranosyl)adenine, as well as compound 6, showed no antimalarial activity.
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000962:Antimalarials / Q000138:chemical synthesis; D002942:Circular Dichroism; D003837:Deoxy Sugars / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D000962:Antimalarials; D003837:Deoxy Sugars; D009705:Nucleosides; D000225:Adenine