- Carba-acyclonucleoside antiherpetic agents
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Ganciclovir 2 and 2'-carba-ganciclovir 5a are anti-viral agents differing structurally only in the replacement of an oxygen by a methylene group and yet expressing their biological properties along mechanistically independent pathways. Methoxy, hydroxy an
- Hannah,Tolman,Karkas,Liou,Perry,Field
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p. 1261 - 1271
(2007/10/02)
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- Synthesis and Antiviral Activity of 9-purines
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Alkylation of 2-amino-6-chloropurine with 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxane (5) provided 2-amino-6-chloro-9-purine (6) in high yield.This aminochloropurine 6 readily converted to the antiviral acyclonucleoside 9-guanine (1) and to its 6-chloro (10), 6-thio (11), 6-alkoxy (12-17), 6-amino (20), and 6-deoxy (21) purine analogues.The guanine derivative 1 was converted to its xanthine analogue 9.Similarly, alkylation of 6-chloropurine with 5 provided a route to 8, the hypoxanthine analogue of 1.Of these 9-substituted purines, the guanine derivative 1 showed the highest activity against herpes simplex virus types 1 and 2 in cell cultures, and in some tests it was more active than acyclovir, with no evidence of toxicity for the cells.A series of monoesters (30-33) and diesters (24-27, 29) of 1 were prepared, and some of these also showed antiherpes virus activity in cell cultures, the most active ester being the dihexanoate 27.
- Harnden, Michael R.,Jarvest, Richard L.,Bacon, Teresa H.,Boyd, Malcolm R.
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p. 1636 - 1642
(2007/10/02)
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