title: Synthesis and anti-HIV evaluation of 3'-triazolo nucleosides.
abstract: A series of hitherto unknown 3'-α-[1,2,3]-substituted triazolo-2',3'-dideoxypyrimidine nucleoside analogues of the anti-HIV 3'-azido-3'-deoxythymidine (AZT) were synthesized through catalyzed alkyne-azide 1,3-dipolar cycloaddition (Huisgen reaction). Those 3'-[1,2,3]-triazolo analogues bearing an azido alkyl chain were evaluated for their anti-HIV activity against HIV-1 in primary human lymphocytes as well as for their cytotoxicity in different cells. None of them inhibit HIV replication (EC(50) > 20 μM); two of them were converted to their triphosphate form to evaluate their HIV-RT inhibition.
authors.affiliation: Institut de Chimie Organique et Analytique, UMR 6005, Université d′Orléans, Orléans, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Roy
authors.forename: Aleksandr
authors.initials: A
authors.lastname: Obikhod
authors.forename: Hong-Wang
authors.initials: HW
authors.lastname: Zhang
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Coats
authors.forename: Brian D
authors.initials: BD
authors.lastname: Herman
authors.forename: Nicolas
authors.initials: N
authors.lastname: Sluis-Cremer
authors.forename: Luigi A
authors.initials: LA
authors.lastname: Agrofoglio
authors.forename: Raymond F
authors.initials: RF
authors.lastname: Schinazi
mesh_terms: D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001386:Azides / Q000737:chemistry; D002460:Cell Line; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D001386:Azides; D009705:Nucleosides; D014230:Triazoles; C514824:reverse transcriptase, Human immunodeficiency virus 1; D054303:HIV Reverse Transcriptase