Institut de Chimie Organique et Analytique, UMR 6005, Université d'Orléans, 45067 Orléans, France.
Eur J Med Chem. 2011 Feb;46(2):778-86. doi: 10.1016/j.ejmech.2010.12.017. Epub 2010 Dec 21.
The synthesis and antiviral evaluation of a series of C5-(1,4- and 1,5-disubstituted-1,2,3-triazolo)-nucleoside derivatives is described. The key steps of this synthesis are regioselective Huisgen's 1,3-dipolar cycloaddition, using either copper-catalyzed azide-alkyne cycloaddition (CuAAC) or ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) under microwave activation. Some compounds among the 5a-l series possess activity against herpes simplex viruses 1 and 2, varicella-zoster virus, human cytomegalovirus and vaccinia virus. Their cytostatic activities were determined against murine leukemia cells, human T-lymphocyte cells and cervix carcinoma cells. Compounds were also evaluated on a wide panel of RNA viruses, including Vesicular stomatitis virus, influenza viruses type A (H1N1 and H3N2) and B in MDCK cell cultures, parainfluenza-3 virus, reovirus-1, Sindbis virus and Punta Toro virus in Vero cell cultures and Vesicular stomatitis, Coxsackie B4 and respiratory syncytial virus, with no specific antiviral effect.
描述了一系列 C5-（1,4-和 1,5-取代-1,2,3-三唑基）-核苷衍生物的合成和抗病毒评估。该合成的关键步骤是区域选择性的 Huisgen 1,3-偶极环加成反应，分别使用铜催化的叠氮-炔环加成（CuAAC）或钌催化的叠氮-炔环加成（RuAAC）在微波激活下进行。5a-l 系列中的一些化合物对单纯疱疹病毒 1 和 2、水痘-带状疱疹病毒、人巨细胞病毒和牛痘病毒具有活性。它们的细胞抑制活性针对鼠白血病细胞、人 T 淋巴细胞和宫颈癌细胞进行了测定。还对包括 MDCK 细胞培养中的水疱性口炎病毒、甲型流感病毒（H1N1 和 H3N2）和 B、副流感-3 病毒、肠道病毒-1、辛德比斯病毒和蓬塔托罗病毒以及 Vero 细胞培养中的水疱性口炎病毒、柯萨奇 B4 和呼吸道合胞病毒的广泛 RNA 病毒进行了评估，没有发现特定的抗病毒作用。
