title: Synthesis of entecavir and its novel class of analogs.
abstract: Due to the slow kinetics of viral clearance and the spontaneous genetic variability of hepatitis B virus (HBV), antiviral therapy of chronic hepatitis B remains a clinical challenge. Entecavir (S.10; a 2'-deoxy carbocyclic guanosine analog with an exo-cyclic double bond on the 5'-position; Fig. 14.7.1) has been approved in the U.S. for the therapy of chronic hepatitis B. Entecavir is synthesized from D-ribose via a key allylic alcohol (S.3) intermediate. This intermediate is also utilized to synthesize entecavir-modified carbocyclic nucleosides S.13, S.15, S.19, and S.22.
authors.affiliation: The University of Georgia College of Pharmacy, Athens, Georgia, USA.
authors.forename: Ravindra K
authors.initials: RK
authors.lastname: Rawal
authors.forename: Uma Sharan
authors.initials: US
authors.lastname: Singh
authors.forename: Srinivas
authors.initials: S
authors.lastname: Gadthula
authors.forename: Chung K
authors.initials: CK
authors.lastname: Chu
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D019694:Hepatitis B, Chronic / Q000188:drug therapy; D006801:Humans; D008956:Models, Chemical; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D012266:Ribose / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D020005:Propanols; C006463:allyl alcohol; C413685:entecavir; D006147:Guanine; D012266:Ribose