title: Synthesis and antiviral evaluation of novel 6'(alpha)-methyl-branched Carbovir analogues.
abstract: A new stereoselective synthesis of 6'-branched Carbovir analogues was accomplished in this study. The introduction of a methyl group in the requisite 6'(alpha)-position was carried out using an ester enolate alkylation (LHMDS, CH3I). The desired cyclopentenol 7 was synthesized via a Felkin-Anh-controlled Grignard addition and ring-closing metathesis using second-generation Grubbs' catalyst. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2, and HCMV, the adenine analogue 12 exhibited moderate antiviral activity against the HCMV.
authors.affiliation: College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
authors.forename: Jin Woo
authors.initials: JW
authors.lastname: Kim
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003587:Cytomegalovirus / Q000187:drug effects; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D015224:Dideoxynucleosides; D009705:Nucleosides; C057503:carbovir