Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus-Reference-Cited by-同舟云学术

Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus

Published:2002-08 Issue:4 Volume:13 Page:251-262
ISSN:2040-2066
Container-title:Antiviral Chemistry and Chemotherapy
language:en
Short-container-title:Antivir Chem Chemother

Author:

Wang Ruifang¹,Kern Earl R²,Zemlicka Jiri¹

Affiliation:

1. Department of Chemistry, Developmental Therapeutics Program, Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, Detroit, Mich., USA

2. Department of Pediatrics, The University of Alabama at Birmingham, Birmingham, Ala. USA

Abstract

Methylenecyclobutane analogues of 2′-deoxyadenosine, 2′-deoxyguanosine and 2′- deoxycytidine, and the corresponding phosphoralaninate pronucleotides comprising adenine and guanine bases, were synthesized as potential antiviral agents. Phosphoralaninate of adenine methylenecyclobutane was a potent inhibitor of replication of Epstein-Barr virus (EBV) in Daudi cell culture. Phosphoralaninate of guanine analogue was inactive but both pronucleotides were substrates for porcine liver esterase. Adenine methylenecyclobutane analogue was deaminated by adenosine deaminase.

Publisher

SAGE Publications

Link

http://journals.sagepub.com/doi/pdf/10.1177/095632020201300406

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