OSO2OCH3 36.1.8

Another way of synthesis of vidarabine that was developed later consists of alkylating of 6-benzamidopurine with 2,3,5-in-O-benzyl-D-arabinofuranosyl chloride using sodium in liquid ammonia. This simultaneously N-debenzylates the sixth position of the purine system and fulfil O-debenzylation of hydroxyl groups of the furanosyl fragment of the molu-cule, giving vidarabine [14].



NH3/ Na

Vidarabine (adenine arabinoside) is the stereoisomer of adenosine. This analog of a purine nucleoside exhibits selective activity against the herpes virus. The ribose residue is replaced with an arabinose residue. Like acyclovir, it turns into mono-, di-, and triphosphate in cells infected by a virus, thus inhibiting DNA polymerase, and correspondingly preventing DNA synthesis of the virus approximately 20-40 times more than in "host" cells. It is easily metabolized to a less active, yet nonetheless antiviral compound—arabinosylhypoxanthine. It has been successfully used for herpetic encephalitis, and for complicated shingles. It is used in the form of eye drops for herpetic keratoconjuctivitis. A synonym of this drug is Vira-A.

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