Fluorocarbocyclic nucleosides: synthesis and antiviral activity of 2'-and 6'-fluorocarbocyclic 2'-deoxyguanosines

AD Borthwick, BE Kirk, K Biggadike…

Index: Borthwick; Kirk; Biggadike; Exall; Butt; Roberts; Knight; Coates; Ryan Journal of Medicinal Chemistry, 1991 , vol. 34, # 3 p. 907 - 914

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Citation Number: 61

Abstract

For comparison, the furanosyl compound 9-(2'-deoxy-2'-fluoro-/3-~ arabinofuranosyl) guanine (17, AF'G) was prepared by coupling 2-amino-6-chloropurine with 2-deoxy-2-fluoro- 3, 5-di-O-benzoyl-a-~-arabinofuranosyl bromide followed by base hydrolysis. The 6'a-fluor0 derivative lld exhibited comparable activity to that of acyclovir (ACV) against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro but was> 30-fold more active than ACV ...