Acetylenic nucleosides. 4. 1-(. beta.-D-Arabinofuranosyl)-5-ethynylcytosine. Improved synthesis and evaluation of biochemical and antiviral properties

…, I Kavai, RA Sharma, S Grill, G Dutschman…

Index: Bobek; Kavai; Sharma; Grill; Dutschman; Cheng Journal of Medicinal Chemistry, 1987 , vol. 30, # 11 p. 2154 - 2157

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Citation Number: 25

Abstract

5-Ethynyl-l-~-~-arabinofuranosylcyt~~ ine (EAC) was prepared from 1-(2, 3, 5-tri-0-acetyl-~- D-arabinofuranosy~) c~ os~ ne by iodination followed by coupling with (trimethylsily1) acetylene and deblocking. At 50 yM, EAC was found to inhibit the in vitro replication of herpes simplex virus type 1 and type 2 by> 99%. EAC also showed activity against a strain of HSV-1 resistant to (E)-5-(2-bromovinyl)-2'-deoxyuridine which has an alteration of the ...