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Antiviral activity of novel 2'-fluoro-6'-methylene-carbocyclic adenosine against wild-type and drug-resistant hepatitis B virus mutants. 2011
Jianing Wang, and
Uma S Singh, and
Ravindra K Rawal, and
Masaya Sugiyama, and
Massaya Sugiyama, and
Jakyung Yoo, and
Ashok K Jha, and
Melissa Scroggin, and
Zhuhui Huang, and
Michael G Murray, and
Rajgopal Govindarajan, and
Yasuhito Tanaka, and
Brent Korba, and
Chung K Chu
The University of Georgia, College of Pharmacy, Athens, GA 30602, USA.
Novel 2'-fluoro-6'-methylene-carbocyclic adenosine (9) was synthesized and evaluated its anti-HBV activity. The titled compound demonstrated significant antiviral activity against wild-type as well as lamivudine, adefovir and double lamivudine/entecavir resistant mutants. Molecular modeling study indicate that the 2'-fluoro moiety by a hydrogen bond, as well as the van der Waals interaction of the carbocyclic ring with the phenylalanine moiety of the polymerase promote the positive binding, even in the drug resistant mutants.
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